Diastereocontrolled Formal Syntheses of (±)-Lepadiformines A, B, and C and the Divergent Synthesis of 2-epi-Lepadiformine C through Unexpected Double Consecutive Epimerizations-Reference-Cited by-同舟云学术

Diastereocontrolled Formal Syntheses of (±)-Lepadiformines A, B, and C and the Divergent Synthesis of 2-epi-Lepadiformine C through Unexpected Double Consecutive Epimerizations

Published:2020-06-25 Issue:14 Volume:85 Page:9051-9063
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Wu Jui-Lin¹,Chiou Wen-Hua¹^ORCID

Affiliation:

1. Department of Chemistry, National Chung-Hsing University, Taichung 402, Taiwan, R.O.C.

Funder

Ministry of Science and Technology

National Chung-Hsing University

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/acs.joc.0c00964

Reference35 articles.

1. Lepadiformine, a new marine cytotoxic alkaloid from Clavelina lepadiformis Müller

2. First Total Synthesis of the Marine Alkaloids (±)-Fasicularin and (±)-Lepadiformine Based on Stereocontrolled Intramolecular Acylnitroso-Diels−Alder Reaction

3. Stereoselective Total Syntheses of the Racemic Form and the Natural Enantiomer of the Marine Alkaloid Lepadiformine via a Novel N-Acyliminium Ion/Allylsilane Spirocyclization Strategy

4. Total Synthesis of the Natural Enantiomer of (â)-Lepadiformine and Determination of Its Absolute Stereochemistry This work was supported in part by a Grant for Private Universities provided by the Ministry of Education, Sports, and Culture of Japan and the Promotion and Mutual Aid Corporation for Private Schools of Japan. We are grateful to Professor J. F. Biard for a sample of natural lepadiformine.

5. Lepadiformine: A Case Study of the Value of Total Synthesis in Natural Product Structure Elucidation

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