Asymmetric synthesis of cytospolides C and D through successful exploration of stereoselective Julia–Kocienski olefination and Suzuki reaction followed by macrolactonization. Issue 21 (27th May 2015)

• Record Type: Journal Article
• Authors: Rej, Rohan Kalyan; Kumar, Rajan; Nanda, Samik
• Is Part Of: Tetrahedron. Volume 71:Issue 21(2015)
• Page Start: 3185
• Page End: 3194
• Publication Date: 2015-05-27
• Subjects: Julia–Kocienski olefination -- Mitsunobu lactonization -- Metal enzyme combined dynamic kinetic resolution (MEDKR) -- Suziki cross coupling reaction -- Asymmetric synthesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.04.014
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Asymmetric total synthesis of two naturally occurring nonenolides cytospolides C (3 ) and D (4 ) was accomplished through successful exploration of stereoselective Julia–Kocienski (JK) olefination reaction for the construction of the required E -olefinic geometry (C4 –C5 ) present in the target molecule. In an alternative approach Suzuki cross coupling reaction of an E -vinylic bromide and an alkylborane species was also efficiently applied to access the macrolactonization precursor. Late stage lactonization through Mitsunobu cyclization afforded the target molecules in good yield. Graphical abstract: