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Literature DB >> 26859526

Collaborative Total Synthesis: Routes to (±)-Hippolachnin A Enabled by Quadricyclane Cycloaddition and Late-Stage C-H Oxidation.

Monica E McCallum¹, Christopher M Rasik², John L Wood¹, M Kevin Brown².

Abstract

Described herein are synthetic efforts toward the synthesis of hippolachnin A. Two independently devised routes from the Brown and Wood groups allowed for the synthesis of hippolachnin A from the unusual starting material, quadricyclane, by harnessing the power of late-stage C-H oxidation. Collaborative union of the best features of the two routes allowed for preparation of the molecule with improved efficiency.

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Year: 2016 PMID： 26859526 PMCID： PMC4866603 DOI： 10.1021/jacs.5b13586

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

26 in total

1. Tandem catalysis: the sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes.

Authors: J Louie; C W Bielawski; R H Grubbs
Journal: J Am Chem Soc Date: 2001-11-14 Impact factor: 15.419

Collaborative Total Synthesis: Routes to (±)-Hippolachnin A Enabled by Quadricyclane Cycloaddition and Late-Stage C-H Oxidation.

1. Tandem catalysis: the sequential mediation of olefin metathesis, hydrogenation, and hydrogen transfer with single-component Ru complexes.

2. Innate and guided C-H functionalization logic.

3. C-H functionalization logic in total synthesis.

4. Directed metal (oxo) aliphatic C-H hydroxylations: overriding substrate bias.

5. A Unified Strategy to Plakortin Pentalenes: Total Syntheses of (±)-Gracilioethers E and F.

Review 6. If C-H bonds could talk: selective C-H bond oxidation.

7. C-H bond functionalization in complex organic synthesis.

Review 8. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

9. N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation.

10. Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.

1. Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.

2. Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.

Review 3. Aliphatic C-H Oxidations for Late-Stage Functionalization.

4. Total Syntheses of (-)-Majucin and (-)-Jiadifenoxolane A, Complex Majucin-Type Illicium Sesquiterpenes.