Stereochemistry of the Robinson-Schoepf reaction. A stereospecific total synthesis of the ladybug defense alkaloids precoccinelline and coccinelline

RV Stevens, AWM Lee

Index: Stevens,R.V.; Lee,A.W.M. Journal of the American Chemical Society, 1979 , vol. 101, p. 7032 - 7035

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Citation Number: 118

Abstract

Abstract: A stereospecific total synthesis of the ladybug defensive alkaloids coccinelline (1) and precoccinelline (2) is presented. A key step in this synthesis involves a Robinson- Schopf type of condensation between amine dialdehyde equivalent 32 and acetone dicarboxylic ester to afford 37. A rationale for this stereochemical course is presented.

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