Enantioselective Total Synthesis of a  trans ‐Hydrindane Rings/Side‐Chain Building‐Block of Vitamin D − Asymmetric Induction in an Acid‐Catalyzed Conjugate‐Addition Reaction | Zendy

Gorobets Evgueni | Zendy; Stepanenko Viatcheslav | Zendy; Wicha Jerzy | Zendy

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Enantioselective Total Synthesis of a trans ‐Hydrindane Rings/Side‐Chain Building‐Block of Vitamin D − Asymmetric Induction in an Acid‐Catalyzed Conjugate‐Addition Reaction

Author(s) -

Gorobets Evgueni,

Stepanenko Viatcheslav,

Wicha Jerzy

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200300611

Subject(s) - enantioselective synthesis , chemistry , conjugate , asymmetric induction , steric effects , catalysis , stereochemistry , optically active , ketene , derivative (finance) , hexanoic acid , medicinal chemistry , organic chemistry , mathematical analysis , mathematics , financial economics , economics

For the enantioselective total synthesis of 1α,25‐dihydroxyvitamin D 3 ( 3 ), we have developed an enantioselective approach to the “northern” portion building‐block 8 , starting from the optically active hexanoic acid derivative 44 , 2‐methylcyclopent‐2‐en‐1‐one ( 10 ) and 1‐(phenylthio)but‐3‐en‐2‐one ( 9 ). The steric course of the addition reaction of homochiral ( S )‐ketene acetals 28 , 40 , 44 and 58 with 10 was examined. We found that in the cases of 28 , 44 and 40 , the reactions occur with high simple and induced (facial) diastereoselectivities. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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