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Synthesis of Gossypol Analogues
Author(s) -
Ognyanov Vassil I.,
Petrov Orlin S.,
Tiholov Emil P.,
Mollov Nikola M.
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720221
Subject(s) - chemistry , gossypol , ring (chemistry) , stereochemistry , organic chemistry , biochemistry
Two gossypol analogues 2a and 2b were synthesized for biological evaluation as male contraceptive agents. The naphthol 8c was prepared by analogy with a known procedure starling from 3‐isopropylcatechol ( 3 ). ( t ‐Bu) 2 O 2 ‐Mediated phenolic coupling of 8c furnished the binaphthol 9c which, after pyrane ring closure, deprotection. and selective bisformylation with SnCl 4 /Cl 2 CHOCH 3 , gave the target compound 2a . The corresponding tetrahydroxy analogue 2b was prepared in a similar way.