aea1dc75bda0fb15dedd36cf796ac08d pmc_31861056.pdf 1165280c27e11dfde108c78ce39b350bcb537347 pmc_31861056.pdf 7383a9a0c58a3325615da11bc42e05ed9bd47fef3dea8c6c9bf7e8de27cdcd65 pmc_31861056.pdf Title: Synthesis and Structural Determination of New Brassinosteroid 24-Nor-5-Cholane Type Analogs Subject: Natural brassinosteroids possess a 22R, 23R configuration that appears essential for biological activity. It is, therefore, interesting to elucidate if the activity of brassinosteroids with a short side chain depends on the C22 configuration. Herein, we describe the synthesis of new brassinosteroids analogs with 24-norcholane type of side chain and R configuration at C22. The initial reaction is the dihydroxylation of a terminal olefin that leads to S/R epimers. Three different methods were tested in order to evaluate the obtained S/R ratio and the reaction yields. The results indicate that Upjohn dihydroxylation is the most selective reaction giving a 1.0:0.24 S/R ratio, whereas a Sharpless reaction leads to a mixture of 1.0:0.90 S/R with 95% yield. Using the latter mixture and following a previous reported method, benzoylated derivatives and both S and R brassinosteroids analogs were synthesized. All synthesized compounds were completely characterized by NMR spectroscopy, and HRMS of new compounds are also given. In conclusion, a synthetic route for preparation of new analogs of brassinosteroids of 24-norcholane type and R configuration at C22 were described. It is expected that this will help to elucidate if a configuration at C22 is a structural requirement for hormonal growth activity in plants. Keywords: synthesis; brassinosteroid; analogues; 24-nor-5-cholane Author: Jocelyn Oyarce, Vanessa Aitken, César González, Karoll Ferrer, Andrés F. Olea, Teodor Parella and Luis Espinoza Catalán Creator: LaTeX with hyperref package Producer: pdfTeX-1.40.19 CreationDate: Tue Dec 17 07:46:36 2019 CET ModDate: Tue Dec 17 07:46:36 2019 CET Tagged: no UserProperties: no Suspects: no Form: none JavaScript: no Pages: 14 Encrypted: no Page size: 595.276 x 841.89 pts (A4) Page rot: 0 File size: 1840371 bytes Optimized: no PDF version: 1.5 name type encoding emb sub uni object ID ------------------------------------ ----------------- ---------------- --- --- --- --------- GQLLGV+URWPalladioL-Ital Type 1 Custom yes yes no 128 0 KIWACN+URWPalladioL-Bold Type 1 Custom yes yes no 129 0 CZOINJ+EURB10 Type 1 Builtin yes yes no 130 0 GIFXFT+VnURWPalladioL-Bold Type 1 Custom yes yes no 131 0 BYCVAQ+URWPalladioL-Roma Type 1 Custom yes yes no 132 0 VVVOUQ+VnURWPalladioL Type 1 Custom yes yes no 133 0 SVVJCD+Rpxr Type 1 Builtin yes yes no 134 0 YWGLGW+Rpxi Type 1 Builtin yes yes no 135 0 VVSYYB+EURM10 Type 1 Builtin yes yes no 136 0 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PageMode: UseNone Outlines: Item: Title: ぉのぴひはつふっぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸲ Item: Title: げづびふぬぴびぜ〴ぜ〰ちのつぜ〴ぜ〰いどびっふびびどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮ㄩ‾㸊⡜㌷㙜㌷㝜〰いどひづっぴぜ〴ぜ〰さばなはとのぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㈩‾㸊⡜㌷㙜㌷㝜〰ぅばはへどつちぴどはのぜ〴ぜ〰ちのつぜ〴ぜ〰こふぢびづぱふづのぴぜ〴ぜ〰くばづのどのでぜ〴ぜ〰はてぜ〴ぜ〰ぅばはへどつづぜ〴ぜ〰げどのでぜ〴ぜ〰どのぜ〴ぜ〰ぁっどつぜ〴ぜ〰きづつどふねぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㌩‾㸊⡜㌷㙜㌷㝜〰ことちひばぬづびびぜ〴ぜ〰ぁびべねねづぴひどっぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㐩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あづのぺはべぬちぴづつぜ〴ぜ〰いづひどぶちぴどぶづびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㔩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あげびぜ〴ぜ〰ぁのちぬはでびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸳ Children: Item: Title: いどひづっぴぜ〴ぜ〰さばなはとのぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㈩‾㸊⡜㌷㙜㌷㝜〰ぅばはへどつちぴどはのぜ〴ぜ〰ちのつぜ〴ぜ〰こふぢびづぱふづのぴぜ〴ぜ〰くばづのどのでぜ〴ぜ〰はてぜ〴ぜ〰ぅばはへどつづぜ〴ぜ〰げどのでぜ〴ぜ〰どのぜ〴ぜ〰ぁっどつぜ〴ぜ〰きづつどふねぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㌩‾㸊⡜㌷㙜㌷㝜〰ことちひばぬづびびぜ〴ぜ〰ぁびべねねづぴひどっぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㐩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あづのぺはべぬちぴづつぜ〴ぜ〰いづひどぶちぴどぶづびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㔩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あげびぜ〴ぜ〰ぁのちぬはでびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸳ Item: Title: ぅばはへどつちぴどはのぜ〴ぜ〰ちのつぜ〴ぜ〰こふぢびづぱふづのぴぜ〴ぜ〰くばづのどのでぜ〴ぜ〰はてぜ〴ぜ〰ぅばはへどつづぜ〴ぜ〰げどのでぜ〴ぜ〰どのぜ〴ぜ〰ぁっどつぜ〴ぜ〰きづつどふねぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㌩‾㸊⡜㌷㙜㌷㝜〰ことちひばぬづびびぜ〴ぜ〰ぁびべねねづぴひどっぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㐩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あづのぺはべぬちぴづつぜ〴ぜ〰いづひどぶちぴどぶづびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㔩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あげびぜ〴ぜ〰ぁのちぬはでびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸳ Item: Title: ことちひばぬづびびぜ〴ぜ〰ぁびべねねづぴひどっぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㐩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あづのぺはべぬちぴづつぜ〴ぜ〰いづひどぶちぴどぶづびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㔩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あげびぜ〴ぜ〰ぁのちぬはでびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸳ Item: Title: こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あづのぺはべぬちぴづつぜ〴ぜ〰いづひどぶちぴどぶづびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㈮㔩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あげびぜ〴ぜ〰ぁのちぬはでびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸳ Item: Title: こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰あげびぜ〴ぜ〰ぁのちぬはでびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳散瑩潮⸳ Item: Title: きちぴづひどちぬびぜ〴ぜ〰ちのつぜ〴ぜ〰きづぴとはつびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㌮ㄩ‾㸊⡜㌷㙜㌷㝜〰ぇづのづひちぬぜ〴ぜ〰ぅへばづひどねづのぴちぬぜ〴ぜ〰きづぴとはつびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㌮㈩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸱ Children: Item: Title: ぇづのづひちぬぜ〴ぜ〰ぅへばづひどねづのぴちぬぜ〴ぜ〰きづぴとはつびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獥捴楯渮㌮㈩‾㸊⡜㌷㙜㌷㝜〰こべのぴとづびどびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸱ Item: Title: こべのぴとづびどびぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸱ Children: Item: Title: さばなはとのぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴ぜ〰はてぜ〴ぜ〰ぁぬにづのづぜ〴ぜ〰〹〮ぜ〴ぜ〰くぢぴちどのどのでぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〲〲〬〲〳〭つどとべつひはへべ〭〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭ぜ〴ぜ〰〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〰ちぜ〵ㅜ〰ぜ〴ぜ〰ちのつぜ〴ぜ〰ぜ〵ぜ〰〲〲げぜ〵ㅜ〰〭〲〲〬〲〳〭つどとべつひはへべ〭〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〰ぢぜ〵ㅜ〰ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸲ Item: Title: ぅばはへどつちぴどはのぜ〴ぜ〰はてぜ〴ぜ〰ぁぬにづのづぜ〴ぜ〰〹〮ぜ〴ぜ〰くぢぴちどのどのでぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〶〭はへは〭〲〲〬〲〳〭づばはへべ〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ちのつぜ〴ぜ〰ぜ〵ぜ〰〱〱ちぜ〵ㅜ〰ぜ〴ぜ〰ちのつぜ〴ぜ〰ぜ〵ぜ〰〲〲げぜ〵ㅜ〰〭〶〭はへは〭〲〲〬〲〳〭づばはへべ〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〱ぢぜ〵ㅜ〰ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸳ Item: Title: くばづのどのでぜ〴ぜ〰はてぜ〴ぜ〰ぅばはへどつづぜ〴ぜ〰げどのでぜ〴ぜ〰はてぜ〴ぜ〰きどへぴふひづぜ〴ぜ〰〱〱ち〯〱〱ぢぜ〴ぜ〰どのぜ〴ぜ〰ぁっどつぜ〴ぜ〰きづつどふね〮ぜ〴ぜ〰くぢぴちどのどのでぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〲〲〬〲〳〭つどとべつひはへべ〭ぜ〴ぜ〰〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〰ちぜ〵ㅜ〰ぜ〴ぜ〰ちのつぜ〴ぜ〰ぜ〵ぜ〰〲〲げぜ〵ㅜ〰〭〲〲〬〲〳〭つどとべつひはへべ〭〶〭はへは〭〲〴〭のはひ〭〵ぜ〴ぜ〰〭っとはぬちの〭〳ぜ〴ぜ〰〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〰ぢぜ〵ㅜ〰ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸴ Item: Title: いどひづっぴぜ〴ぜ〰ぁびべねねづぴひどっぜ〴ぜ〰ことちひばぬづびびぜ〴ぜ〰いどとべつひはへべぬちぴどはのぜ〴ぜ〰はてぜ〴ぜ〰ぁぬにづのづぜ〴ぜ〰〹〮ぜ〴ぜ〰くぢぴちどのどのでぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〲〲〬〲〳〭つどとべつひはへべ〭ぜ〴ぜ〰〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〰ちぜ〵ㅜ〰ぜ〴ぜ〰ちのつぜ〴ぜ〰ぜ〵ぜ〰〲〲げぜ〵ㅜ〰〭〲〲〬〲〳〭つどとべつひはへべ〭〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〭べぬぜ〴ぜ〰ちっづぴちぴづぜ〴ぜ〰ぜ〵ぜ〰〱〰ぢぜ〵ㅜ〰ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸵ Item: Title: こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〲〲〭とべつひはへべ〭〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〬〲〳〭つどべぬぜ〴ぜ〰〳〭ちっづぴちぴづぜ〴ぜ〰〲〳〭ぢづのぺはちぴづぜ〴ぜ〰ぜ〵ぜ〰〵ぜ〵ㅜ〰〬ぜ〴ぜ〰ぜ〵ぜ〰〲〲げぜ〵ㅜ〰〭〲〲〭とべつひはへべ〭〶〭はへは〭〲〴〭のはひ〭〵〭っとはぬちの〭〳〬〲〳〭つどべぬぜ〴ぜ〰〳〭ちっづぴちぴづぜ〴ぜ〰〲〳〭ぢづのぺはちぴづぜ〴ぜ〰ぜ〵ぜ〰〷ぜ〵ㅜ〰ぜ〴ぜ〰ちのつぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〶〭はへは〭〲〴〭のはひ〭ぜ〴ぜ〰〵〭っとはぬちの〭〳〬〲〲〬〲〳〭ぴひどべぬぜ〴ぜ〰〳〭ちっづぴちぴづぜ〴ぜ〰〲〲〬〲〳〭つどぢづのぺはちぴづぜ〴ぜ〰ぜ〵ぜ〰〸ぜ〵ㅜ〰ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸶ Item: Title: こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〲〴〭のはひ〭〵〭っとはぬちの〭〶〭はへは〭〳〬〲〲〬〲〳〭ぴひどべぬぜ〴ぜ〰〳〭ちっづぴちぴづぜ〴ぜ〰〲〲〬〲〳〭つどぢづのぺはちぴづぜ〴ぜ〰ぜ〵ぜ〰〸ぜ〵ㅜ〰ぜ〴ぜ〰てひはねぜ〴ぜ〰〵ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸷ Item: Title: こべのぴとづびどびぜ〴ぜ〰はてぜ〴ぜ〰ぜ〵ぜ〰〲〲こぜ〵ㅜ〰〭〳〬〲〲〬〲〳〭ぴひどとべつひはへべ〭〲〴〭のはひ〭〵〭っとはぬちの〭〶〭はのづぜ〴ぜ〰ぜ〵ぜ〰〴ぜ〵ㅜ〰ぜ〴ぜ〰てひはねぜ〴ぜ〰〵ぜ〴〩਼㰠⽓ 䝯呯 䐠⡳畢獵扳散瑩潮⸳⸲⸸ Item: Title: 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