Enantio‐ and Diastereocontrolled Total Synthesis of (+)‐Strictifolione

Abstract

A concise and practical enantioselective synthesis of (+)-strictifolione has been achieved in high diastereomeric excess using Jacobsen's hydrolytic kinetic resolution, proline-

Bicyclic Oxygen Heterocycles from γ,δ‐Unsaturated Alcohols: Synthetic Targets Inspired by Blepharocalyxin D

“…To extend the utility of this method, a route for the enantioselective synthesis of (+)-g,d-unsaturated alcohol 39 was developed (Scheme 10). The known [14] (S)-allylic alcohol 34 was prepared by a Keck allylation of dihydrocinnamaldehyde, [15] and was then protected as silyl ether 35. After hydroboration of the alkene with 9-borabicyclo[3.3.1]nonane (9-BBN)/H 2 O 2 , the resultant primary alcohol 36 was oxidized under Swern conditions to give aldehyde 37 in 68 % yield over the 2 steps.…”

Bicyclic Oxygen Heterocycles from γ,δ‐Unsaturated Alcohols: Synthetic Targets Inspired by Blepharocalyxin D

“…To extend the utility of this method, a route for the enantioselective synthesis of (+)‐γ,δ‐unsaturated alcohol 39 was developed (Scheme ). The known14 ( S )‐allylic alcohol 34 was prepared by a Keck allylation of dihydrocinnamaldehyde,15 and was then protected as silyl ether 35 . After hydroboration of the alkene with 9‐borabicyclo[3.3.1]nonane (9‐BBN)/H 2 O 2 , the resultant primary alcohol 36 was oxidized under Swern conditions to give aldehyde 37 in 68 % yield over the 2 steps.…”

Recent Advances in the Stereoselective Total Synthesis of Natural Pyranones Having Long Side Chains

“…Its earlier syntheses were mentioned by Macro et al [12]. Recently, a large number of new syntheses of strictifolione (176) have been reported [92,[103][104][105][106][107][108][109].…”