Synthesis of optically active homotryptophan and its oxygen and sulfur analogues

Goswami, K.; Paul, S.; Bugde, S.T.; Sinha, S.

Synthesis of optically active homotryptophan and its oxygen and sulfur analogues

Goswami, K.; Paul, S.; Bugde, S.T.; Sinha, S.

Source : Tetrahedron. 68(1); 2012; 280-286.

URI: http://dx.doi.org/10.1016/j.tet.2011.10.055
http://irgu.unigoa.ac.in/drs/handle/unigoa/2712

Date: 2012

Document Type: Journal article

Abstract:

D-Homotryptophan and its sulfur analogue have been synthesized by Sonogashira coupling between 3-iodoheteroarenes and ethynyloxazolidine followed by reduction of triple bond and oxidation of alcohol to acid. L-Homotryptophan and its oxygen analogue have been synthesized from silylated internal alkyne using Larock's heteroannulation as the key reaction. The allcynyloxazolidines were synthesized from L-serine and L-glutamic acid, respectively.

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