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Literature DB >> 10823221

Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement.

A B Smith¹, P R Verhoest, K P Minbiole, J J Lim.

Abstract

[formula: see text] In this, the first of two letters, we outline our overall strategy for the total synthesis of phorboxazoles A (1) and B (2), rare oxazole-containing macrolides possessing extraordinary antimitotic activity, and describe the assembly of a C(3-19) subtarget (-)-5 for the total synthesis of phorboxazole A. The synthesis of (-)-5 was achieved in 15 linear steps (12% overall yield), exploiting a modification of the Petasis-Ferrier rearrangement to construct the C(11-15) cis-tetrahydropyran. Dimethylaluminum chloride (Me2AlCl) proved to be the Lewis acid of choice for the Petasis-Ferrier rearrangement.

Entities: Chemical

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Year: 1999 PMID： 10823221 DOI： 10.1021/ol990830l

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

8 in total

1. Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

Authors: Arun K Ghosh; Xu Cheng
Journal: Tetrahedron Lett Date: 2012-05-16 Impact factor: 2.415

2. Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

Authors: Amos B Smith; Chris Sfouggatakis; Christina A Risatti; Jeffrey B Sperry; Wenyu Zhu; Victoria A Doughty; Takashi Tomioka; Dimitar B Gotchev; Clay S Bennett; Satoshi Sakamoto; Onur Atasoylu; Shohei Shirakami; David Bauer; Makoto Takeuchi; Jyunichi Koyanagi; Yasuharu Sakamoto
Journal: Tetrahedron Date: 2009-09-15 Impact factor: 2.457

3. (+)-Sorangicin A: evolution of a viable synthetic strategy.

Authors: Amos B Smith; Shuzhi Dong; Richard J Fox; Jehrod B Brenneman; John A Vanecko; Tomohiro Maegawa
Journal: Tetrahedron Date: 2011-12-23 Impact factor: 2.457

4. Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors: Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal: Org Lett Date: 2002-04-04 Impact factor: 6.005

5. Evolution of the total synthesis of (-)-okilactomycin exploiting a tandem oxy-cope rearrangement/oxidation, a Petasis-Ferrier union/rearrangement, and ring-closing metathesis.

Authors: Amos B Smith; Todd Bosanac; Kallol Basu
Journal: J Am Chem Soc Date: 2009-02-18 Impact factor: 15.419

Phorboxazole synthetic studies. 1. Construction of a C(3-19) subtarget exploiting an extension of the Petasis-Ferrier rearrangement.

1. Synthesis of Functionalized 4-Methylenetetrahydropyrans by Oxidative Activation of Cinnamyl or Benzyl Ethers.

2. Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

3. (+)-Sorangicin A: evolution of a viable synthetic strategy.

4. Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

5. Evolution of the total synthesis of (-)-okilactomycin exploiting a tandem oxy-cope rearrangement/oxidation, a Petasis-Ferrier union/rearrangement, and ring-closing metathesis.

6. Studies of stereocontrolled allylation reactions for the total synthesis of phorboxazole A.

Review 7. The Petasis-Ferrier rearrangement: developments and applications.

8. Silyl enol ether Prins cyclization: diastereoselective formation of substituted tetrahydropyran-4-ones.