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Letter

Caylobolide A, a Unique 36-Membered Macrolactone from a Bahamian Lyngbya majuscula^†

Supporting Info

John B. MacMillan and Tadeusz F. Molinski*

Department of Chemistry, University of California, Davis, California 95616

Org. Lett., 2002, 4 (9), pp 1535–1538

DOI: 10.1021/ol025759p

Publication Date (Web): April 6, 2002

†

This paper is dedicated to Professor D. John Faulkner (Scripps Institute of Oceanography) on the occasion of his 60th birthday.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, tfmolinski@ucdavis.edu

Abstract

A new 36-membered macrolactone, (25S,27S,29S,33S)-caylobolide A, was isolated from the Bahamian cyanobacterium Lyngbya majuscula. The structure of caylobolide contains an unprecedented repeated unita contiguous pentad of 1,5 diolsand a 1,3,5-triol. The relative steroechemistry of the 1,3,5-triol was determined using Kishi's Universal NMR database, and absolute stereochemistry at C25,27,29 and C33 were determined by Mosher's analysis. Caylobolide A exhibited in vitro cytotoxicity against human colon tumor cells (IC₅₀ HCT 116, 9.9 μM).