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Convergent Total Synthesis of (−)-Cyclopamine

Sofiadis, Manolis ; Xu, Dongmin ; Rodriguez, Anthony J. ; Nissl, Benedikt ; Clementson, Sebastian LU orcid ; Petersen, Nadia Nasser and Baran, Phil S. (2023) In Journal of the American Chemical Society 145(40). p.21760-21765
Abstract
A concise and enantioselective total synthesis of the Veratrum
alkaloid cyclopamine is disclosed. This highly convergent synthesis with
a 16-step longest linear sequence (LLS) was enabled by a de novo synthesis of the trans-6,5-heterobicycle
via a strain-inducing halocyclization process, a key Tsuji–Trost
cyclization to construct the fully substituted, spirocyclic THF motif
with exquisite diastereocontrol, and a late-stage ring-closing
metathesis (RCM) reaction to forge the central tetrasubstituted olefin.
Please use this url to cite or link to this publication:
author
; ; ; ; ; and
publishing date
type
Contribution to journal
publication status
published
in
Journal of the American Chemical Society
volume
145
issue
40
pages
6 pages
publisher
The American Chemical Society (ACS)
external identifiers
  • scopus:85175587053
ISSN
1520-5126
DOI
10.1021/jacs.3c09085
language
English
LU publication?
no
additional info
PMID: 37782691
id
2ddfe2db-8f28-4f1b-97ab-84dfb31ea83d
date added to LUP
2025-08-06 19:36:23
date last changed
2025-08-28 12:42:15
@article{2ddfe2db-8f28-4f1b-97ab-84dfb31ea83d,
  abstract     = {{A concise and enantioselective total synthesis of the <i>Veratrum</i> <br>
alkaloid cyclopamine is disclosed. This highly convergent synthesis with<br>
 a 16-step longest linear sequence (LLS) was enabled by a <i>de novo</i> synthesis of the <i>trans</i>-6,5-heterobicycle<br>
 via a strain-inducing halocyclization process, a key Tsuji–Trost <br>
cyclization to construct the fully substituted, spirocyclic THF motif <br>
with exquisite diastereocontrol, and a late-stage ring-closing <br>
metathesis (RCM) reaction to forge the central tetrasubstituted olefin.}},
  author       = {{Sofiadis, Manolis and Xu, Dongmin and Rodriguez, Anthony J. and Nissl, Benedikt and Clementson, Sebastian and Petersen, Nadia Nasser and Baran, Phil S.}},
  issn         = {{1520-5126}},
  language     = {{eng}},
  number       = {{40}},
  pages        = {{21760--21765}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{Journal of the American Chemical Society}},
  title        = {{Convergent Total Synthesis of (−)-Cyclopamine}},
  url          = {{http://dx.doi.org/10.1021/jacs.3c09085}},
  doi          = {{10.1021/jacs.3c09085}},
  volume       = {{145}},
  year         = {{2023}},
}