English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Pericyclic reactions in nature: evidence for a spontaneous [1.7]-hydrogen shift and an 8pe electrocyclic ring closure in the biosynthesis of olefinic hydrocarbons from marine brown algae (Phaeophyceae)

Pohnert, G., & Boland, W. (1994). Pericyclic reactions in nature: evidence for a spontaneous [1.7]-hydrogen shift and an 8pe electrocyclic ring closure in the biosynthesis of olefinic hydrocarbons from marine brown algae (Phaeophyceae). Tetrahedron, 50(34), 10235-10244. doi:10.1016/S0040-4020(01)81756-7.

Item is

Files

show Files
hide Files
:
BOL272.pdf (Publisher version), 0B
 
File Permalink:
-
Name:
BOL272.pdf
Description:
-
OA-Status:
Visibility:
Restricted (Max Planck Institute for Chemical Ecology, MJCO; )
MIME-Type / Checksum:
application/octet-stream
Technical Metadata:
Copyright Date:
-
Copyright Info:
-
License:
-

Locators

show

Creators

show
hide
 Creators:
Pohnert, Georg1, Author           
Boland, Wilhelm1, Author           
Affiliations:
1External Organizations, ou_persistent22              

Content

show
hide
Free keywords: -
 Abstract: The stereochemistry of the algal C11H16 hydrocarbon giffordene 3 results from a spontaneous [1,7]-sigmatropic hydrogen shift of the thermolabile (1,3Z,5Z,8Z)-undecatetraene 8. An 8 pi e electrocyclisation of (1,3Z,5Z,7E)-nonatetraene 9 is substantiated for the biosynthesis of 7-methylcyclooctatriene 5, a product of the Mediterranean brown alga Cutleria multifida. Low temperature syntheses (-30 degrees C) of the thermolabile precursors 8 and 9 are described. The activation energies of the [1,7]-sigmatropic hydrogen shift 8-->3 (E(a) = 67.4 kJ mol(-1)) and of the 8 pi e electrocyclisation 9-->5 (E(a) = 59.4 kJ mol(-1)) are the lowest values currently known for natural pericyclic reactions.

Details

show
hide
Language(s):
 Dates: 1994
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: Other: BOL272
DOI: 10.1016/S0040-4020(01)81756-7
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Tetrahedron
  Other : Tetrahedron
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 50 (34) Sequence Number: - Start / End Page: 10235 - 10244 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/954925448773