4.7 Article

Isolation and Synthesis of Azuriaplysins A and B, Bromoditerpenes with an a-Methylene Carbonyl from the Sea Hare Aplysia kurodai

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 85, Issue 8, Pages 2082-2089

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.2c00476

Keywords

-

Funding

  1. JSPS KAKENHI [20H02865]
  2. Nissan Chemical Corporation Award in Synthetic Organic Chemistry, Japan
  3. Support for Pioneering Research Initiated by the Next Generation (SPRING)

Ask authors/readers for more resources

Two new bromoditerpenes, azuriaplysins A (1) and B (2), were isolated from the sea hare Aplysia kurodai. Their relative stereostructures were determined by NMR analysis, and their absolute stereostructures were determined through total synthesis. Azuriaplysin B (2) and its enantiomer exhibited moderate cytotoxicity against HeLa S3 cells.
New bromoditerpenes having an alpha-methylene carbonyl structure, azuriaplysins A (1) and B (2), were isolated from the sea hare Aplysia kurodai. Their relative stereostructures were determined based on one-and two-dimensional NMR spectroscopic analysis. In addition, the absolute stereostructures were determined by the total synthesis of both enantiomers of azuriaplysins A (1) and B (2), the key points of which were bromocyclization of farnesol and optical resolution of a key intermediate. Azuriaplysin B (2) and its enantiomer exhibited moderate cytotoxicity against HeLa S3 cells.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.7
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available