1.
J Org Chem
; 82(1): 438-460, 2017 01 06.
Article
in English
| MEDLINE
| ID: mdl-27936701
ABSTRACT
Synthesis of the macrolactone depsipeptide aetheramide A was attempted by three different approaches. The first approach to form the macrolactone involving macrolactonization to form the C1-C21 bond and the second approach using a ring-closing metathesis (RCM) strategy to form the C10-C11 olefinic bond failed. The third approach starting from R-mandelic acid, involving the RCM reaction to install the C18-C19 ring junction, was successful in assembling the macrolactone.
Subject(s)
Depsipeptides/chemical synthesis , Ethers/chemical synthesis , Depsipeptides/chemistry , Ethers/chemistry , Molecular Conformation
2.
J Org Chem
; 79(3): 1461-6, 2014 Feb 07.
Article
in English
| MEDLINE
| ID: mdl-24392655
ABSTRACT
Total synthesis of 10-membered lactone (+)-seimatopolide A is presented from furfural. Key reactions in the present strategy include the effective use of furan as a E-but-2-ene-1,4-dione surrogate, Nagao acetate aldol reaction, and Shiina lactonization.