Organic Letters p. 9071 - 9074 (2020)
Update date:2022-08-11
Topics:
Martin, Stephen F.
Wang, Zhipeng
The first total syntheses of (±)-melicolones A and B, which have a unique and densely functionalized framework derived from a rearranged prenylated acetophenone, were accomplished in 12.3% combined overall yield. The concise and divergent synthesis of these two natural products, which were isolated in racemic form, was achieved in a longest linear sequence requiring only 9 steps (11 total steps) and 8 isolated intermediates using commercially available starting materials. This approach, which might enable access to all tetracyclic melicolones, features the highly regioselective (16:1) and diastereoselective (15:1) dipolar cycloaddition of a carbonyl ylide generated by the unusual cyclization of a rhodium carbene with the carbonyl oxygen atom of an aliphatic aldehyde. This cycloaddition proceeds with dominant steric control to give a highly functionalized oxabicycloheptane core. Stereoselective enolate alkylation led to a prenylated intermediate that underwent an intramolecular aldol reaction to give the penultimate tricyclic intermediate. Tandem epoxidation of the pendant prenyl group followed by a regioselective, acid-catalyzed cyclization delivered (±)-melicolones A and B.
View Morejintan yufan Medicine Raw materials Co.,Ltd.
Contact:86-519-82808282
Address:6th,Jincheng Huangzhuang
website:http://www.weichichem.com
Contact:+8613912949432
Address:Fine Chemical Industrial Base,Wujiang town,He County,Anhui China.
Contact:+86-20-62802632;62802633
Address:Room 330 GIGCAS Building,No.511 Kehua Street,Tianhe District
Xinji City Taida Sinopec Co., Ltd.
Contact:0086-311-85341278
Address:No.6, Nanhua Road,Xinji City Road,Hebei Province,China
Ningbo Tide Imp. & Exp. Co., Ltd.
Contact:+86-571-8993 7933; +86-571-8993 6453
Address:7/F Anno Domini Building, Tower South, 8 Qiu Shi Road,Hangzhou,China.
Doi:10.1149/1.1370967
(2001)Doi:10.1016/j.cattod.2016.03.024
(2016)Doi:10.1021/op0601058
(2006)Doi:10.1002/anie.201103742
(2011)Doi:10.1016/j.tet.2008.06.005
(2008)Doi:10.1002/adsc.201600673
(2016)