Total Synthesis of Brevetoxin A: Part 1: First Generation Strategy and Construction of BCD Ring System

• Published in: Chemistry : a European journal Vol. 5; no. 2; pp. 599 - 617
• Main Authors: Nicolaou, K. C., Bunnage, Mark E., McGarry, Daniel G., Shi, Shuhao, Somers, Patricia K., Wallace, Paul A., Chu, Xin-Jie, Agrios, Konstantinos A., Gunzner, Janet L., Yang, Zhen
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.1999; WILEY‐VCH Verlag; Wiley
• Subjects: Brevetoxin A; Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; Synthetic methods; Total synthesis; brevetoxin A; RED TIDE; TOXINS; PTYCHODISCUS-BREVIS; total synthesis; CYCLIC ETHERS; EPOXIDE OPENINGS; TETRAHYDROPYRAN SYSTEMS; TECHNOLOGY; EFFICIENT; synthetic methods; STEREOCONTROLLED SYNTHESIS; GYMNODINIUM-BREVE

Dissection of brevetoxin A at the nine‐membered ring site (ring E) formed the basis of the first generation strategy for the total synthesis of this molecule. Unfortuately the planned hydroxy dithioketal cyclization to form the crucial nonacene did not proceed as anticipated and this approach was di...