615284-84-9Relevant academic research and scientific papers
Total synthesis and structural elucidation of azaspiracid-1. Construction of key building blocks for originally proposed structure
Nicolaou,Pihko, Petri M.,Bernal, Federico,Frederick, Michael O.,Qian, Wenyuan,Uesaka, Noriaki,Diedrichs, Nicole,Hinrichs, Juergen,Koftis, Theocharis V.,Loizidou, Eriketi,Petrovic, Goran,Rodriquez, Manuela,Sarlah, David,Zou, Ning
, p. 2244 - 2257 (2007/10/03)
Syntheses of the three key building blocks (65, 98, and 100) required for the total synthesis of the proposed structure of azaspiracid-1 (1a) are described. Key steps include a TMSOTf-induced ring-closing cascade to form the ABC rings of tetracycle 65, a neodymium-catalyzed internal aminal formation for the construction of intermediate 98, and a Nozaki-Hiyama-Kishi coupling to assemble the required carbon chain of fragment 100. The synthesized fragments, obtained stereoselectively in both their enantiomeric forms, were expected to allow for the construction of all four stereoisomers proposed as possible structures of azaspiracid-1 (1a-d), thus allowing the determination of both the relative and absolute stereochemistry of the natural product.
Total synthesis of the proposed azaspiracid-1 structure, Part 1: Construction of the enantiomerically pure C1-C20, C21-C27, and C28-C40 fragments
Nicolaou,Li, Yiwei,Uesaka, Noriaki,Koftis, Theocharis V.,Vyskocil, Stepan,Ling, Taotao,Govindasamy, Mugesh,Qian, Wenyuan,Bernal, Federico,Chen, David Y.-K.
, p. 3643 - 3648 (2007/10/03)
As a build-up to the synthesis of the proposed structure of azaspiracid, both enantiomers of fragments 2, 3, and 4 were synthesized stereoselectively. Piv=pivaloyl, PFP = pentafluorophenyl, Teoc = 2-(trimethylsilyl)ethoxycarbonyl, TES = triethylsilyl.
