Total synthesis and structural elucidation of azaspiracid-1 : construction of key building blocks for originally proposed structure

Article


Nicolaou, K., Pihko, P., Bernal, F., Frederick, M., Qian, W., Uesaka, N., Diedrichs, N., Hinrichs, J., Koftis, T., Loizidou, E., Petrovic, G., Rodriquez, M., Sarlah, D. and Zou, N. 2006. Total synthesis and structural elucidation of azaspiracid-1 : construction of key building blocks for originally proposed structure. Journal of the American Chemical Society. 128 (7), pp. 2244-2257. https://doi.org/10.1021/ja0547477
TypeArticle
TitleTotal synthesis and structural elucidation of azaspiracid-1 : construction of key building blocks for originally proposed structure
AuthorsNicolaou, K., Pihko, P., Bernal, F., Frederick, M., Qian, W., Uesaka, N., Diedrichs, N., Hinrichs, J., Koftis, T., Loizidou, E., Petrovic, G., Rodriquez, M., Sarlah, D. and Zou, N.
Abstract

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.

PublisherACS
JournalJournal of the American Chemical Society
ISSN0002-7863
Publication dates
Print28 Jan 2006
Publication process dates
Deposited06 Mar 2015
Output statusPublished
Digital Object Identifier (DOI)https://doi.org/10.1021/ja0547477
LanguageEnglish
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