Synthesis of Gossypol Analogues

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)2O2‐Mediated phenolic coupling of 8c furnished the binaphthol 9c which, after pyrane r...

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Veröffentlicht in:	Helvetica chimica acta 1989-03, Vol.72 (2), p.353-360
Hauptverfasser:	Ognyanov, Vassil I., Petrov, Orlin S., Tiholov, Emil P., Mollov, Nikola M.
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	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)2O2‐Mediated phenolic coupling of 8c furnished the binaphthol 9c which, after pyrane ring closure, deprotection. and selective bisformylation with SnCl4/Cl2CHOCH3, gave the target compound 2a. The corresponding tetrahydroxy analogue 2b was prepared in a similar way.
ISSN:	0018-019X 1522-2675
DOI:	10.1002/hlca.19890720221