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Studies directed toward the total synthesis of azaspiracid. Construction of the C1–C19 carbon backbone and synthesis of the C10, C13 nonnatural transoidal bisspirocyclic ring system

✍ Scribed by Rich G Carter; David E Graves

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 104 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01211-4

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✦ Synopsis

The efficient entry to the C 1 -C 19 carbon backbone of azaspiracid is outlined utilizing a key Julia coupling strategy. Spirocyclization of a C 12 sulfone substrate induced formation of the unprecedented, nonnatural transoidal bisspiroketal. Construction of the bisspirocyclic array at C 10 and C 13 , in the absence of the C 12 sulfone, led to formation of the cisoidal orientation of the bisspirocycle, with the nonnatural stereochemistry at C 13 .

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