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A short synthesis of (±)-laurene: mechanistic reinvestigation in palladium-catalyzed cycloreductions of 1,6-enynes

✍ Scribed by Chang Ho Oh; Je Wook Han; Joo Sung Kim; Sung Yong Um; Hyung Hoon Jung; Won Hyung Jang; Ho Shik Won

Book ID: 104211034
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 102 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01484-2

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✦ Synopsis

Two palladium-catalyzed cycloreduction strategies have been applied for the synthesis of laurene. Palladium-catalyzed cyclizations of 1,6-enynes initially form the corresponding alkylpalladium intermediates. While triethylsilane could directly reduce the intermediates to lead to the corresponding cycloreduced products, the intermediates in the presence of even excess formic acid underwent b-elimination to yield the dienes that were further reduced at the less hindered olefins to yield the cycloreduced products.

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