Literature DB >> 16591739

Total synthesis of the racemic form of the second juvenile hormone (methyl 12-homojuvenate) from the cecropia silk moth.

W S Johnson1, S F Campbell, A Krishnakumaran, A S Meyer.   

Abstract

Methyl cis-10-epoxy-3,7,11-trimethyl-trans,trans-2,6-tridecadienoate has been stereoselectively synthesized in 12 steps starting from methyl trans-gamma-bromo-beta,beta-dimethylacrylate and 1-acetyl-1-methylcyclopropane. The final product proved to be identical with the second, less abundant juvenile hormone (methyl 12-homojuvenate) isolated from the Cecropia silk moth. The biological activities of the compound were evaluated in various insects.

Entities:  

Year:  1969        PMID： 16591739      PMCID： PMC223604          DOI： 10.1073/pnas.62.4.1005

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  4 in total

1.  The two juvenile hormones from the cecropia silk moth.

Authors:  A S Meyer; H A Schneiderman; E Hanzmann; J H Ko
Journal:  Proc Natl Acad Sci U S A       Date:  1968-07       Impact factor: 11.205

2.  Juvenile hormone activity of structurally unrelated compounds.

Authors:  H A Schneiderman; A Krishnakumaran; V G Kulkarni; L Friedman
Journal:  J Insect Physiol       Date:  1965-12       Impact factor: 2.354

3.  Prothoracotrophic activity of compounds that mimic juvenile hormone.

Authors:  A Krishnakumaran; H A Schneiderman
Journal:  J Insect Physiol       Date:  1965-12       Impact factor: 2.354

4.  A highly purified preparation of juvenile hormone from the silk moth Hyalophora cecropia L.

Authors:  A S Meyer; H A Schneiderman; L I Gilbert
Journal:  Nature       Date:  1965-04-17       Impact factor: 49.962
  4 in total
  1 in total

1.  Absolute configuration of Cecropia juvenile hormone.

Authors:  A S Meyer; E Hanzmann; R C Murphy
Journal:  Proc Natl Acad Sci U S A       Date:  1971-09       Impact factor: 11.205
  1 in total

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