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Literature DB >> 16608366

Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy.

Amos B Smith¹, Eugen F Mesaros, Emmanuel A Meyer.

Abstract

A convergent stereocontrolled total synthesis of (-)-kendomycin (1) has been achieved. The synthesis proceeds with a longest linear sequence of 21 steps, beginning with commercially available 2,4-dimethoxy-3-methylbenzaldehyde (12). Highlights of the synthesis include an effective Petasis-Ferrier union/rearrangement tactic to construct the sterically encumbered tetrahydropyran ring, a ring-closing metathesis to generate the C(4a-13-20a) macrocycle, an effective epoxidation/deoxygenation sequence to isomerize the C(13,14) olefin, and a biomimetic quinone-methide-lactol assembly to complete the synthesis.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 16608366 DOI： 10.1021/ja060369+

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

12 in total

1. 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

2. Phorboxazole Synthetic Studies: Design, Synthesis and Biological Evaluation of Phorboxazole A and Hemi-Phorboxazole A Related Analogues.

Authors: Amos B Smith; Anne-Marie L Hogan; Zhuqing Liu; Thomas M Razler; Regina M Meis; Brandon I Morinaka; Tadeusz F Molinski
Journal: Tetrahedron Date: 2011-07-08 Impact factor: 2.457

3. Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

Authors: Kevin P C Minbiole
Journal: J Antibiot (Tokyo) Date: 2016-03-02 Impact factor: 2.649

10. Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: catalysts for efficient Z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis.

Authors: Chenbo Wang; Fredrik Haeffner; Richard R Schrock; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2013-01-10 Impact factor: 15.336

Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy.

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

2. Phorboxazole Synthetic Studies: Design, Synthesis and Biological Evaluation of Phorboxazole A and Hemi-Phorboxazole A Related Analogues.

3. Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

4. C6-C8 bridged epothilones: consequences of installing a conformational lock at the edge of the macrocycle.

Review 5. Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin.

Review 6. Prins-type macrocyclizations as an efficient ring-closing strategy in natural product synthesis.

7. Total synthesis of dolabelide C: a phosphate-mediated approach.

8. Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.

Review 9. The Petasis-Ferrier rearrangement: developments and applications.

10. Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: catalysts for efficient Z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis.