| Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclization. | |
| | |
MedLine Citation:
|
PMID: 22469969 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
The synthesis of the macrolactone core of (+)-neopeltolide has been achieved. The key synthetic strategy involves the highly diastereoselective synthesis of the 2,6-cis-disubstituted tetrahydropyran ring by a transannular cyclization of δ-hydroxy alkene using mercuric trifluoroacetate. Two of the six stereocenters C-5 and C-11 were realized from l-malic acid, while the remaining stereocenters C-3 (Sharpless asymmetric epoxidation), C-7 (transannular cyclization), C-9 (regioselective epoxide opening) and C-13 (chelation controlled reduction) were derived by asymmetric synthesis. The macrolactone ring was synthesized by macrocyclization using a RCM protocol. |
| | |
Authors:
|
Gangavaram V M Sharma; Sheri Venkat Reddy; Kallaganti V S Ramakrishna |
Related Documents
:
|
22793789 - Iron catalyzed asymmetric oxyamination of olefins. 22887699 - Enantioselective h-bond-directing approach for trienamine-mediated reactions in asymmet... 22296409 - Silver as an example of the applications of photochemistry to the synthesis and uses of... 6331449 - Transition metals mediate enzymatic inactivation caused by favism-inducing agents. 21866909 - Synthesis of antimitotic thioglycosides: in vitro and in vivo evaluation of their antic... 22898799 - Electrochemically shape-controlled synthesis of trapezohedral platinum nanocrystals wit... 20853879 - α-chloro-β,γ-ethylenic esters: enantiocontrolled synthesis and substitutions. 8020129 - Steroidal constituents from the underground parts of reineckea carnea and their inhibit... 20361769 - Oh radical initiated oxidation of 1,3-butadiene: isomeric selective study of the domina... |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2012-4-2 |
Journal Detail:
|
Title: Organic & biomolecular chemistry Volume: - ISSN: 1477-0539 ISO Abbreviation: - Publication Date: 2012 Apr |
Date Detail:
|
Created Date: 2012-4-3 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
|
Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India. esmvee@iict.res.in. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Normative cultural values and the experiences of mexican-american mothers in the neonatal intensive ...
Next Document: Magnetization reversal process at atomic scale in systems with itinerant electrons.