Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
An Asymmetric Synthesis of the BC Ring System of 8-Epitaxoids by Way of Intramolecular Aldol and Successive Stereoselective Methylation Reactions
Teruaki MukaiyamaIsamu ShiinaHayato IwadareMasahiro SaitohKoji NishimuraToshihiro NishimuraNaoto OhkawaHiroki SakohKatsuyuki Saitoh
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1996 Volume 25 Issue 6 Pages 483-484

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Abstract

Optically active 1α-allyl-1β,11β-benzylidenedioxy-2α,10β-bis(benzyloxy)-7β,9β-isopropylidenedioxy-8α,12,12-trimethyl-4-methylenebicyclo[6.4.0]dodecane (2)1 which corresponds to BC ring system of 8-epitaxoids was prepared in high yield form ketoaldehyde 8 via intramolecular aldol cyclization and succesive stereoselective methylation reactions. The ketoaldehyde 8 was synthesized from 8-membered ring compound 3 by stereoselective Michael addition using higher-order cuprate.

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© 1996 The Chemical Society of Japan
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