Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization

Synthesis of the southern FGHI ring system of azaspiracid-1 and investigation into the controlling elements of C28- and C36-ketalization

Zhou, XT ; Lu, L ; Furkert, Daniel ; Wells, CE ; Carter, RG
Identifier: http://hdl.handle.net/2292/13744
Issue Date: 2006
Reference: Angewandte Chemie (International ed.) 45(45):7622-7626 2006
Rights: Copyright: Wiley-VCH Verlag GmbH & Co.
Rights (URI): https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm

Abstract:

Heading south: An efficient approach to the FGHI southern ring system of azaspiracid-1 is disclosed. Each of the eight stereogenic centers is generated with excellent diastereoselectivity. In addition, the stereochemical outcome of the ketalization steps could be controlled by careful selection of the conditions. Teoc=2-(trimethylsilyl)ethoxycarbonyl; TMS=trimethylsilyl; TIPS=triisopropylsilyl; Bn=benzyl.

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DOI: 10.1002/anie.200603353
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