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Approaches to the synthesis of 12-thiasteroids: synthesis of B-nor-6,12-bisthiaestra-1,3,5(10),8,14-pentaen-17-one.

✍ Scribed by S.R. Ramadas; P.Ch. Chenchaiah; J.Appa Rao; S. Kumaresan

Publisher: Elsevier Science
Year: 1983
Tongue: French
Weight: 261 KB
Volume: 24
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87880-6

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✦ Synopsis

A new approach to the total synthesis of 12-thiasteroids has led to the synthesis of B-nor-6,12-bisthiaestra-l,3,5(10),8,14-~e~taen-l7_one~~

A very careful survey of literature on heterosteroids -and in particular thiasteroids7 points out the fact that there has been no report on t1,e partial or total synthesis of 12-thiasteroids till date. An isolated report8 appeared in 1977, describing the synthesis of B-nor-6-aza-12-thia-3-methoxyestra-1,3,5(10),8-tetraen-12-dioxide-17~~1. This approach' is only applicable to this system as it is primarily based on Fischer indole rearrangement reaction.

The present paper reports the development of a new synthetic plan towards the construction of a 12-thiasteroid skeleton involving only a few steps. This method has a wider applicability and can be extended towards the total synthesis of 12-thiaaromatic, heteroaromatic and even non-aromatic steroids (u Scheme I) , utilizing the most appropriately substituted mercaptomethyl derivatives such as la, lb and 14.

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