Studies Toward Synthesis of Tetracyclic Core of Daphmanidin A–Type Alkaloids

Abstract

A stereoselective approach to spiro-annulated bicyclo[2.2.2]octane ring system related to the tetracyclic skeleton of daphmanidin A–type alkaloids is described. Ring-closing metathesis, Wacker oxidation, and aldol condensation are key features ofour approach. An interesting steric effect on aldol condensation has also been observed.

GRAPHICAL ABSTRACT

Keywords:

• Alkylation
• bicyclo[2.2.2]octane
• ring-closing metathesis

ACKNOWLEDGMENT

We thank D. Mhatre for crystal structure determination.

SUPPLEMENTAL MATERIAL

Full experimental details and ¹H and ¹³C spectra for this article can be accessed on the publisher’s website.