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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 14
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Synthetic Communications Review

Stereoselective total synthesis of paecilomycin E and F and its two congeners Cochliomycin C and 6-epi-Cochliomycin C

Sudhakar KadariDepartment of Chemistry, Osmania University, Hyderabad, India; Correspondence[email protected]
ORCID Iconhttp://orcid.org/0000-0001-5902-2093View further author information
ORCID Icon,
Hemasri YerrabellyDepartment of Chemistry, Osmania University, Hyderabad, India; View further author information
,
Jayaprakash Rao YerrabellyDepartment of Chemistry, Osmania University, Hyderabad, India; View further author information
,
Thirupathi GogulaDepartment of Chemistry, Osmania University, Hyderabad, India; View further author information
,
Yadaiah GoudDepartment of Chemistry, Osmania University, Hyderabad, India; View further author information
,
Gangadhar ThalariDepartment of Chemistry, Osmania University, Hyderabad, India; View further author information
&
Sai Reddy DodaNatural Products Chemistry Division, CSIR – Indian Institute of Chemical Technology, Hyderabad, IndiaCorrespondence[email protected]
View further author information
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Pages 1867-1875 | Received 30 Jan 2018, Published online: 18 Jun 2018
 
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Abstract

An efficient and concise approach to the total synthesis of Paecilomycins E (1) and F (2), Cochliomycin C (4) and 6-epi-Cochliomycin C (3) is described. The synthesis involves novel route to the synthesis of Paecilomycin E and F and further conversion to Cochliomycin C and 6-epi-Cochliomycin C. Olefin metathesis and base promoted macro lactonization being the key reactions followed by chlorination to achieve target Cochliomycin C and 6-epi-Cochliomycin C.

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Additional information

Funding

KSR thanks the DST-SERB (Young scientist File: CS-138/012), New Delhi, India, for financial support.

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