TOTAL SYNTHESIS OF (+ -)-TAZETTINE

Authors
RIGBY JH CAVEZZA A HEEG MJ
Citation
Jh. Rigby et al., TOTAL SYNTHESIS OF (+ -)-TAZETTINE, Journal of the American Chemical Society, 120(15), 1998, pp. 3664-3670
Citations number
66
Categorie Soggetti
Chemistry
Journal title
Journal of the American Chemical Society → ACNP
ISSN journal
00027863
Volume
120
Issue
15
Year of publication
1998
Pages
3664 - 3670
Database
ISI
SICI code
0002-7863(1998)120:15<3664:TSO(->2.0.ZU;2-5
Abstract
The total synthesis of (+/-)-tazettine (1) has been achieved in 16 ste ps from commercially available piperonyl alcohol in 11% overall yield. The crucial quaternary center was assembled by a novel [4+1] cycloadd ition between dimethoxycarbene and beta-aryl vinyl isocyanate (4). Sam arium diiodide conditions were employed to reduce the enamide unsatura tion in the [2]benzopyrano[3,4-c]hydroindole intermediate 19 to compou nd 20 exhibiting a cis-AB ring fusion.