✦ LIBER ✦

Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide. Complete reversal of stereoselectivity in reduction of 2-vinyl aldols with / without trimethylsilyl directing group

✍ Scribed by Keisuke Suzuki; Mayumi Miyazawa; Masato Shimazaki; Gen-ichi Tsuchihashi

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 253 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)85441-6

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✦ Synopsis

Stereo-divergent asymmetric total synthesis of avenaciolide and isoavenaciolide was achieved via 1.2-rearrangement

of chiral epoxyalcohol derivatives. where complete reversal of stereoselectivity with / without the TMS-directing group in the reduction of Z-vinyl aldols was used as the key branching point.