A convergent approach to swinholide A. Stereoselective construction of the C3–C17fragment of swinholide A
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 9,p. 1147-1150
- https://doi.org/10.1039/c39940001147
Abstract
A strategy for a total synthesis of the cytotoxic dimeric macrolide swinholide A (1, Scheme 1) is outlined and a stereoselective construction of the suitably functionalized C3–C17 fragment 4, starting with building blocks 6, 7, 9 and 10 is described.Keywords
This publication has 41 references indexed in Scilit:
- Molecular conformation of swinholide A, a potent cytotoxic dimeric macrolide from the Okinawan marine sponge Theonella swinhoei: x-ray crystal structure of its diketone derivativeThe Journal of Organic Chemistry, 1991
- Absolute stereostructure of swinholide A, a potent cytotoxic macrolide from the Okinawan marine sponge Theonella swinhoeiJournal of the American Chemical Society, 1990
- Marine natural products. XXIV. The absolute stereostructure of misakinolide A, a potent cytotoxic dimeric macrolide from an Okinawan marine sponge Theonella sp.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- Marine natural products. XXIII. Three new cytotoxic dimeric macrolides, swinholides B and C and isoswinholide A, congeners of swinholide A, from the Okinawan marine sponge Theonella swinhoei.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- Marine natural products. XXII. The absolute stereostructure of swinholide A, a potent cytotoxic dimeric macrolide from the Okinawa marine sponge Theonella swinhoei.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- Chiral synthesis via organoboranes. 21. Allyl- and crotylboration of .alpha.-chiral aldehydes with diisopinocampheylboron as the chiral auxiliaryThe Journal of Organic Chemistry, 1989
- Retrosynthetic and synthetic chemistry on amphotericin B. Synthesis of C(1)–C(20) and C(21)–C(38) fragments and construction of the 38-membered macrocycleJournal of the Chemical Society, Chemical Communications, 1986
- Large-ring lactones by internal ketophosphonate cyclizationsThe Journal of Organic Chemistry, 1979
- Simple Method for the Esterification of Carboxylic AcidsAngewandte Chemie International Edition in English, 1978
- Applications of Diisobutylaluminium Hydride (DIBAH) and Triisobutylaluminium (TIBA) as Reducing Agents in Organic SynthesisSynthesis, 1975