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Approach toward the total synthesis of orevactaene. Part 1: Assembly of the contiguous trisubstituted olefin component

✍ Scribed by Michael G. Organ; Svetoslav Bratovanov

Book ID: 104210767
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 192 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01189-8

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✦ Synopsis

An approach to the conjugated polyene chain component of orevactaene is reported. A modular approach has been devised to link the two stereocentre-containing ends of the structure together via a trisubstituted ole®n-template. Key to the success of this approach is an ecient `one pot' lithium/halogen exchange, boron/lithium exchange, borate ester saponi®cation, and cross-coupling sequence to provide two contiguous trisubstituted ole®ns with absolute stereo-and regiocontrol in excellent overall yield. These results have paved the way for a parallel synthesis approach to prepare all 16 possible stereoisomers of orevactaene so that the relative and absolute stereochemistry of this compound can be determined.

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