Second generation total synthesis of azaspiracids-1, -2 and -3

Article


Nicolaou, K., Frederick, M., Loizidou, E., Petrovic, G., Cole, K., Koftis, T. and Yamada, Y. 2006. Second generation total synthesis of azaspiracids-1, -2 and -3. Chemistry: an Asian Journal. 1 (1-2), pp. 245-263. https://doi.org/10.1002/asia.200600059
TypeArticle
TitleSecond generation total synthesis of azaspiracids-1, -2 and -3
AuthorsNicolaou, K., Frederick, M., Loizidou, E., Petrovic, G., Cole, K., Koftis, T. and Yamada, Y.
Abstract

The naturally occurring but scarce marine neurotoxins azaspiracids-1, -2, and -3 have been synthesized from five key building blocks by a convergent strategy that involved dithiane and Stille coupling reactions. The ABCD fragments were constructed through a cascade reaction involving deprotection/self-assembly of the precursors, while the FGHI fragment was forged by a neodymium triflate-induced cyclization. The final ring closure (ring G) was achieved, after the union of all fragments, through an iodoetherification reaction followed by reductive removal of the facilitating iodine residue. These improved, second-generation routes confirm the absolute structures and render all three azaspiracids readily available for biological studies.

PublisherWiley
JournalChemistry: an Asian Journal
ISSN1861-4728
Publication dates
Print17 Jul 2006
Publication process dates
Deposited06 Mar 2015
Output statusPublished
Digital Object Identifier (DOI)https://doi.org/10.1002/asia.200600059
LanguageEnglish
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