Synthesis, Conformational Analysis, and Stereoselective Reduction of 14-Membered Ring 3-Keto Lactones

Neeland, Edward G.; Ounsworth, J. P.; Sims, Russel J.; Weiler, Larry

doi:10.1021/jo00103a034

Cited by 17 publications

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“…112 Other work using a peripheral control approach in the context of epoxidation been carried out by Mulzer and Weiler as well. 113,114 We were interested in extending this type of approach to the hydrogenation of a substrate similar to diene 4.2, with the western macrocycle already in place to dictate facial preference and provide the correct relative stereochemistry between C7 and C9 (Scheme 50). While this tactic provided confidence in potentially securing a cis relationship between C7 and C9, we were unsure of the diastereofacial selectivity of the hydrogenation of the C2-C3 olefin.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angew Chem Int Ed

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angew Chem Int Ed

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“…113,114 We were interested in extending this type of approach to the hydrogenation of a substrate similar to diene 4.2, with the western macrocycle already in place to dictate facial preference and provide the correct relative stereochemistry between C7 and C9 (Scheme 50). While this tactic provided confidence in potentially securing a cis relationship between C7 and C9, we were unsure of the diastereofacial selectivity of the hydrogenation of the C2-C3 olefin.…”

mentioning

confidence: 99%

Total Synthesis of (±)‐Haliclonacyclamine C

Smith

Sulikowski

2010

Angewandte Chemie

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Total Synthesis of Maoecrystal V

Zhang

Lin

Shao

et al. 2014

Chemistry An Asian Journal

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Maoecrystal V (1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herb Isodon eriocalyx in 2004 by Sun et al.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC50 value of 20 ng mL(-1) . Significant research efforts have been devoted to the synthesis of maoecrystal V because of its intriguing biological properties, rarity in nature, and complex structural features. Herein, we describe our recent investigations, which have culminated in the total synthesis of (±)-maoecrystal V. The current strategy involved three key steps for the successful construction of the key tetrahydrofuran oxa-bridge skeleton, including a Wessely oxidative dearomatization, a novel intramolecular Diels-Alder reaction, and a Rh(II) -catalyzed O - H insertion reaction.

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Synthesis, Conformational Analysis, and Stereoselective Reduction of 14-Membered Ring 3-Keto Lactones

Cited by 17 publications

References 0 publications

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of (±)‐Haliclonacyclamine C

Total Synthesis of Maoecrystal V

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