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Radical [3 + 2]-annulation of divinylcyclopropanes: Rapid synthesis of complex meloscine analogs

Zhang, H and Jeon, KO and Hay, EB and Geib, SJ and Curran, DP and Laporte, MG (2014) Radical [3 + 2]-annulation of divinylcyclopropanes: Rapid synthesis of complex meloscine analogs. Organic Letters, 16 (1). 94 - 97. ISSN 1523-7060

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A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed. © 2013 American Chemical Society.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Zhang, H
Jeon, KO
Hay, EB
Geib, SJgeib@pitt.eduGEIB0000-0002-9160-7857
Curran, DPcurran@pitt.eduCURRAN
Laporte, MG
Date: 3 January 2014
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 16
Number: 1
Page Range: 94 - 97
DOI or Unique Handle: 10.1021/ol403078e
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Cyclization; Cyclopropanes--chemical synthesis; Cyclopropanes--chemistry; Models, Molecular; Molecular Structure; Polycyclic Compounds--chemical synthesis; Polycyclic Compounds--chemistry; Quinolines--chemical synthesis; Quinolines--chemistry
Other ID: NLM NIHMS547519, NLM PMC3910537
PubMed Central ID: PMC3910537
PubMed ID: 24313360
Date Deposited: 23 Jul 2015 14:36
Last Modified: 02 Feb 2019 15:57


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