56020-70-3Relevant 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.
Total synthesis of diplodialides C and D
Ramanujan, Vyasabhattar,Kumar, Chebolu Naga Sesha Sai Pavan
, p. 332 - 340 (2019/01/03)
A highly convergent, stereoselective total synthesis of diplodialides C and D is described. The protocol involves the use of regioselective ring opening of a chiral epoxide, sequential double alkylation of 1,3-dithiane with a bromide and a chiral epoxide,
A concise stereoselective total synthesis of diplodialide C
Pratapareddy, Bommareddy,Sreenivasulu, Reddymasu,Hatti, Islavathu,Venkata Basaveswara Rao, Mandava,Raju, Rudraraju Ramesh
, p. 1921 - 1926 (2015/10/29)
An asymmetric total synthesis of diplodialide C has been achieved starting from commercially available homoallylic alcohol. Regioselective opening of the chiral epoxide, cross-metathesis reaction, and Yamaguchi macrolactonization were used as the key step
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.
