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Deceptive Complexity in Formation of Cleistantha-8,12-diene.

Authors :
Liang J
Merrill AT
Laconsay CJ
Hou A
Pu Q
Dickschat JS
Tantillo DJ
Wang Q
Peters RJ
Source :
Organic letters [Org Lett] 2022 Apr 15; Vol. 24 (14), pp. 2646-2649. Date of Electronic Publication: 2022 Apr 06.
Publication Year :
2022

Abstract

A barley diterpene synthase (HvKSL4) was found to produce (14 S )-cleistantha-8,12-diene ( 1 ). Formation of the nearly planar cyclohexa-1,4-diene configuration leaves the ring poised for aromatization, but necessitates a deceptively complicated series of rearrangements steered through a complex energetic landscape, as elucidated here through quantum chemical calculations and labeling studies.

Subjects

Subjects :
Plant Leaves
Diterpenes

Details

Language :
English
ISSN :
1523-7052
Volume :
24
Issue :
14
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
35385666
Full Text :
https://doi.org/10.1021/acs.orglett.2c00680