Ring opening of benzoxazinones: An improved and efficient synthesis of clavatustides A & B. Issue 35 (30th August 2017)

• Record Type: Journal Article
• Authors: Chettu, Suresh Kumar; Konidena, Lakshmi Narayana Sharma; Korupolu, Raghu Babu; Kameswara Rao, N.S.; Doddipalla, Raju; Gandham, Hima Bindu; Guduru, Ramakrishna
• Is Part Of: Tetrahedron letters. Volume 58:Issue 35(2017)
• Page Start: 3418
• Page End: 3420
• Publication Date: 2017-08-30
• Subjects: Clavatustide A & B -- Ring opening -- Benzoxazinones -- Cyclodepsipetides -- Anticancer; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.07.059
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: An alternative method for the esterification of α-hydroxyesters has been developed. Ring opening of benzoxazinones with α-hydroxy esters was demonstrated. Synthesis of clavatustides A and B was achieved in 4 steps with good overall yield. Both enantiomers or clavatustides A and B synthesized using the newly developed method. Abstract: Ag2 O mediated esterification of ( R )- tert -butyl 2-hydroxy-3-phenylpropanoate has been realized via the effective ring opening of benzoxazinones that resulted in the efficient synthesis of cyclodepsipeptides clavatustides A and B and their enantiomers in very good overall yields.