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A short and convenient way to produce the Taxol A-ring utilizing the Shapiro reaction

Olli P. Törmäkangas, +3 more
- 11 Mar 2002 - 
- Vol. 58, Iss: 11, pp 2175-2181
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TLDR
In this paper, a Taxol A-ring building block was converted in three simple steps to various arenesulfonylhydrazones and then to the target molecule with the Shapiro reaction.
About: 
This article is published in Tetrahedron.The article was published on 2002-03-11 and is currently open access. It has received 27 citations till now. The article focuses on the topics: Shapiro reaction.

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Citations
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Journal ArticleDOI

The taiwaniaquinoids: a review.

George Majetich, +1 more
- 26 Jan 2010 - 
TL;DR: This review covers the literature from the discovery of the first taiwaniaquinoid in 1995 until June 2009 and a detailed discussion of 12 published syntheses of members of this family of natural products is presented.
Journal ArticleDOI

The organocatalytic three-step total synthesis of (+)-frondosin B

Maud Reiter, +3 more
- 07 Jun 2010 - 
TL;DR: A combination of X-ray crystallographic data, deuterium labeling, and chemical correlation studies provides further evidence as to the correct absolute stereochemical assignment of (+)-frondosin B.
Journal ArticleDOI

Concise, Stereoselective Approach to the Spirooxindole Ring System of Citrinadin A

Martin Pettersson, +2 more
- 06 Oct 2007 - 
TL;DR: The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter using a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.
Journal ArticleDOI

Olefin Metathesis Catalysts Containing N,N′-Diamidocarbenes

Jonathan P. Moerdyk, +1 more
- 30 Mar 2011 - 
TL;DR: In this article, a series of Ru-based olefin metathesis catalysts containing N,N′-diamidocarbenes (DACs) were synthesized and studied.
Journal ArticleDOI

Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization

Keisuke Fukaya, +15 more
- 26 May 2015 - 
TL;DR: A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described and SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function is described.
References
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Journal ArticleDOI

Concise synthesis of taxol a-ring components: Remote diastereoselective additions of alkenyl lithiums to aldehydes

Christopher G. Frost, +3 more
- 16 Dec 1996 - 
TL;DR: The acid chloride 6 provides access to 7 (R,S and S,S) which upon bromine-lithium exchange undergoes remarkably highly diastereoselective additions to aldehydes; 7 is also readily elaborated into the acctal 10.
Journal ArticleDOI

New synthesis of a taxol A-ring system.

Polla Magnus, +1 more
- 26 Mar 1993 - 
TL;DR: The optically active taxol A-ring unit 3 was synthesized in 11 steps from 2-isopropyl-2-propenol as mentioned in this paper, where the stereogenic centers were introduced via the asymmetric glyoxylate-ene reaction and the Sharpless asymmetric epoxidation reaction.
Journal ArticleDOI

Mixture of mechanisms in the reaction of tosylhydrazones with alkyllithium reagents

Robert Shapiro, +1 more
- 01 Jul 1974 - 
Journal ArticleDOI

Siamyl Glyoxylate as an Efficient Enophile in the Lewis Acid Mediated Glyoxylate Ene-Reaction with Allylic Ethers. Application to the Synthesis of a Taxol A-Ring Subunit

Johan Wennerberg, +2 more
- 12 Dec 1997 - 
TL;DR: Siamyl glyoxylate (1a) proved to be an effective enophile in the glyxylate ene-reaction with the allylic ether 2a, which was earlier used for the synthesis of the A-ring subunit of taxol.
Journal ArticleDOI

A short synthesis of the A-ring of taxol

Esko Karvinen, +1 more
- 03 Jul 1995 - 
TL;DR: A short synthesis of the taxol A-ring building block starting from an inexpensive mixture of E- and Z- citrals is described in this paper, where the synthesis is extended to include an E-and Z-citrals.
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Kyriacos C. Nicolaou, +12 more
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Novel synthesis method for natural product isomer (-)-6-epi-Porantheridine

Wang Xiaoji, +6 more

A new synthetic route to TTF-vinylogues

T. Imakubo, +3 more
- 01 Mar 2001 - 

Novel synthesis method of natural product (-)-Porantheridine

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