Total Synthesis and Structure Confirmation of (E) and (Z)‑Ocellenyne

The (E/Z)-ocellenynes are C15 dibrominated Laurencia natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne, which, in combinat...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 24; no. 50; pp. 9174 - 9178
Main Authors Hicks, Harry B., Brown, Daniel S., Sam Chan, Hau Sun, Sousa, Bruno A., Christensen, Kirsten E., Burton, Jonathan W.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.12.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Density Functional Theory
Laurencia - chemistry
Letter
Magnetic Resonance Spectroscopy
Molecular Structure
Physical Sciences
Science & Technology
REASSIGNMENT
SODIUM-BOROHYDRIDE
ETHANOL SOLUTION
HYDROGENATION
NATURAL-PRODUCTS
ORIGIN CHEMISTRY
CONVENIENT
EFFICIENT
LAUREFURENYNES
METATHESIS
Online AccessGet full text

Cover

More Information
Summary:The (E/Z)-ocellenynes are C15 dibrominated Laurencia natural products whose structures have been subject to several reassignments on the basis of extensive NMR analysis, biosynthetic postulates, and DFT calculations. Herein, we report the synthesis of both (E)- and (Z)-ocellenyne, which, in combination with single crystal X-ray diffraction studies, allows their absolute configuration to be established and defines the configuration of the syn-12,13-dibromide as being (S, S) in keeping with their proposed biogenesis from the (6S, 7S)-laurediols.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c03524