56020-71-4Relevant articles and documents
A Polyketide Cyclase That Forms Medium-Ring Lactones
Gao, De-Wei,Jamieson, Cooper S.,Wang, Gaoqian,Yan, Yan,Zhou, Jiahai,Houk,Tang, Yi
supporting information, p. 80 - 84 (2021/01/13)
Medium-ring lactones are synthetically challenging due to unfavorable energetics involved in cyclization. We have discovered a thioesterase enzyme DcsB, from the decarestrictine C1 (1) biosynthetic pathway, that efficiently performs medium-ring lactonizations. DcsB shows broad substrate promiscuity toward linear substrates that vary in lengths and substituents, and is a potential biocatalyst for lactonization. X-ray crystal structure and computational analyses provide insights into the molecular basis of catalysis.
Stereoselective synthesis of (+)-diplodialides-B, C and a formal synthesis of (+)-diplodialide-A by ring-closing metathesis approach
Sharma,Reddy, K. Laxmi
, p. 3197 - 3202 (2007/10/03)
Stereoselective synthesis of diplodialides-B and C and the formal synthesis of diplodialide-A are reported. A combination of Jacobsen's hydrolytic kinetic resolution and Sharpless epoxidation is used for the creation of two stereogenic centers, while a ring-closing metathesis strategy was used for the construction of the lactone ring.