Prev. Article Next Article Table of Contents

Communication

Total Synthesis of (±)-Haouamine A

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

PDF/HTML,
figures/images,
references and tables,
(where available)

Phil S. Baran* and Noah Z. Burns

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037

J. Am. Chem. Soc., 2006, 128 (12), pp 3908–3909

DOI: 10.1021/ja0602997

Publication Date (Web): March 4, 2006

Section:

Alkaloids

Abstract

The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Citing Articles

View all 39 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 18 ACS Journal articles (5 most recent appear below).

Semipinacol Rearrangement in Natural Product Synthesis
Zhen-Lei Song, Chun-An Fan, and Yong-Qiang Tu
Chemical Reviews2011 111 (11), 7523-7556
- Semipinacol Rearrangement in Natural Product Synthesis
  Zhen-Lei Song, Chun-An Fan, and Yong-Qiang Tu
  Chemical Reviews2011 111 (11), 7523-7556
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Use of a Tandem Prins/Friedel–Crafts Reaction in the Construction of the Indeno-Tetrahydropyridine Core of the Haouamine Alkaloids: Formal Synthesis of (−)-Haouamine A
Erik Fenster, Charlie Fehl, and Jeffrey Aubé
Organic Letters2011 13 (10), 2614-2617
- Use of a Tandem Prins/Friedel–Crafts Reaction in the Construction of the Indeno-Tetrahydropyridine Core of the Haouamine Alkaloids: Formal Synthesis of (−)-Haouamine A
  Erik Fenster, Charlie Fehl, and Jeffrey Aubé
  Organic Letters2011 13 (10), 2614-2617
  A tandem Prins/Friedel–Crafts reaction useful for the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids and a formal synthesis of (−)-haouamine A are described.
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
N-Heterocyclic Carbene-Catalyzed (4 + 2) Cycloaddition/Decarboxylation of Silyl Dienol Ethers with α,β-Unsaturated Acid Fluorides
Sarah J. Ryan, Lisa Candish, and David W. Lupton
Journal of the American Chemical Society2011 133 (13), 4694-4697
- N-Heterocyclic Carbene-Catalyzed (4 + 2) Cycloaddition/Decarboxylation of Silyl Dienol Ethers with α,β-Unsaturated Acid Fluorides
  Sarah J. Ryan, Lisa Candish, and David W. Lupton
  Journal of the American Chemical Society2011 133 (13), 4694-4697
  Herein we report the first all-carbon N-heterocyclic carbene-catalyzed (4 + 2) cycloaddition. The reaction proceeds with α,β-unsaturated acid fluorides and silyl dienol ethers and produces 1,3-cyclohexadienes with complete diastereocontrol (dr >20:1) ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Microwave Assisted Synthesis of Bridgehead Alkenes
Leah Cleary, Hoseong Yoo, and Kenneth J. Shea
Organic Letters2011 13 (7), 1781-1783
- Microwave Assisted Synthesis of Bridgehead Alkenes
  Leah Cleary, Hoseong Yoo, and Kenneth J. Shea
  Organic Letters2011 13 (7), 1781-1783
  A new, concise method to synthesize triene precursors for the type 2 intramolecular Diels−Alder reaction has been developed. Microwave irradiation of the trienes provides a convenient method for the synthesis of bridgehead alkenes. Higher yields, shorter ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Total Synthesis of Sporolide B and 9-epi-Sporolide B
K. C. Nicolaou, Jianhua Wang, Yefeng Tang and Lorenzo Botta
Journal of the American Chemical Society2010 132 (32), 11350-11363
- Total Synthesis of Sporolide B and 9-epi-Sporolide B
  K. C. Nicolaou, Jianhua Wang, Yefeng Tang and Lorenzo Botta
  Journal of the American Chemical Society2010 132 (32), 11350-11363
  The total synthesis of the structurally unique secondary metabolite sporolide B (1b) is described. The total synthesis of 1b was developed on the basis of preliminary studies that revealed the reactivity of an appropriate o-quinone as a diene system ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links