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Vitamin D: Enantioselective Synthesis of (3a R, 4 R, 7a S )‐4‐Hydroxy‐7a‐methylperhydro‐1‐indenone, a Suitable CD‐Ring Fragment
Author(s) -
Van Gool Michiel,
Vandewalle Maurits
Publication year - 2000
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 - 10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.0.co;2-x
Subject(s) - chemistry , enantioselective synthesis , stereochemistry , ketone , hydroboration , total synthesis , formal synthesis , ethylenedioxy , triol , ring (chemistry) , decalin , methyl ketone , diol , organic chemistry , alkyl , catalysis
A practical synthesis of trans ‐hydrindanone 5a from (+)‐Wieland−Miescher ketone 8 is described. The target molecule 5a is a suitable precursor for the synthesis of analogues of 1α,25‐dihydroxyvitamin D 3 modified at C‐16, C‐17 or C‐20. During the total synthesis it was found that hydroboration of (1,1)‐ethylenedioxy‐8a‐methyl‐1,2,3,4,6,7,8,8a‐octahydronaphthalene (11) leads to a cis ‐decalin 13 instead of the literature reported trans ‐fusion.