Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone

Jhillu S. Yadav; Ragam Nageshwar Rao; Begari Prem Kumar; Ragam Somaiah; Kontham Ravindar; Basi V. Reddy; Ahamad Al Khazim Al Ghamdi; Ahmad Alkhazim Al Ghamdi

doi:10.1055/s-0030-1260190

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Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone

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Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone

Jhillu S. Yadav, Ragam Nageshwar Rao, Begari Prem Kumar, Ragam Somaiah, Kontham Ravindar, Basi V. Reddy, Ahamad Al Khazim Al Ghamdi and Ahmad Alkhazim Al Ghamdi

Synthesis (Stuttgart), Vol.2011(19), pp.3168-3172

01/10/2011

DOI: https://doi.org/10.1055/s-0030-1260190

Abstract

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Abstract An efficient and concise stereoselective total synthesis of naturally occurring (-)-CIS-aerangis lactone and (-)-CIS-cognac lactone is described. The Sharpless asymmetric epoxidation of a primary allylic alcohol and TBSOTf-mediated intramolecular hydride transfer of a chiral epoxy alcohol have been successfully utilized for the construction of a key precursor with SYN-aldol stereochemistry using a non-aldol pathway.

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Title: Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone
Creators - without role: Jhillu S. Yadav - Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, yadavpub@iict.res.in
Ragam Nageshwar Rao - Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, yadavpub@iict.res.in
Begari Prem Kumar - Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, yadavpub@iict.res.in
Ragam Somaiah - Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, yadavpub@iict.res.in
Kontham Ravindar - Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, yadavpub@iict.res.in
Basi V. Reddy - Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, yadavpub@iict.res.in
Ahamad Al Khazim Al Ghamdi - Engineer Abdullah Bagshan for Bee Research, King Saudi University, Saudi Arabia
Ahmad Alkhazim Al Ghamdi - King Saud University
Publication Details: Synthesis (Stuttgart), Vol.2011(19), pp.3168-3172
Identifiers: 9949640208331
Academic Unit: King Saud University
Language: English
Resource Type: Journal article