Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydro­benzo[e]azulenes

Abstract

Tricyclic keto‐diols have been synthesized from 2‐cyclopenten‐1‐one in a three‐step annulation procedure. The importance of aryl ring electronics and steric contributions and the choice of Lewis acid were investigated for the final cyclization step. An unexpected cyclization product was identified, suggesting multiple mechanisms for the cyclization process.

A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes

“…q, J = 7.8 Hz, 2H), 1.70 (s, 3H), 1.58 (s, 3H); 13 1-Methoxy-3-(4-methylpent-3-en-1-yl)benzene (7d). Following the general procedure for the formation of trisubstituted alkenes using (CH 3 ) 2 CHPPh 3 I 6 (3.8 g, 8.8 mmol, 1.8 equiv), THF (10 mL), n BuLi (3.5 mL, 2.5 M in hexanes, 8.8 mmol, 1.8 equiv), and 3-(3methoxyphenyl)propanal 33 (0.8 g, 4.9 mmol, 1.0 equiv) gave alkene 7d (0.55 g, 59%) as a colorless oil. 10.14469/hpc/6318.…”