Synthesis of the core structure of apicularen a by transannular cyclization

Sven M Kühnert; Martin E Maier

doi:10.1021/ol017261d

Synthesis of the core structure of apicularen a by transannular cyclization

Org Lett. 2002 Feb 21;4(4):643-6. doi: 10.1021/ol017261d.

Authors

Sven M Kühnert¹, Martin E Maier

Affiliation

¹ Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany.

PMID: 11843612
DOI: 10.1021/ol017261d

Abstract

[reaction: see text] An approach to the macrocyclic core of apicularen A is described. Thus, cross-coupling of the aryl triflate 7 with the vinylstannane 19 provided the styrene 20. Deprotection led to the dihydroxy acid 22. Through a size-selective macrolactonization, the 12-membered macrolactone 23 was obtained. Treatment of 24 with N-phenyl selenophthalimide gave the desired trans-pyran 24. This approach might parallel the biosynthetic pathway.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Cyclization
Enzyme Inhibitors / chemical synthesis*
Indicators and Reagents
Models, Molecular
Molecular Conformation
Proton-Translocating ATPases / antagonists & inhibitors*

Substances

Bridged Bicyclo Compounds, Heterocyclic
Enzyme Inhibitors
Indicators and Reagents
apicularen A
Proton-Translocating ATPases