Efficient stereoselective synthesis of all geometrical isomers of 
heptadeca-11,13-dienes

Svatoš, Aleš; Saman, D.

doi:10.1135/cccc19971457

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Efficient stereoselective synthesis of all geometrical isomers of heptadeca-11,13-dienes

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

Svatoš, A., & Saman, D. (1997). Efficient stereoselective synthesis of all geometrical isomers of heptadeca-11,13-dienes. Collection of Czechoslovak Chemical Communications, 62(9), 1457-1467. doi:10.1135/cccc19971457.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-0F3A-2

Abstract

All geometrical isomers of heptacosa-11,13-dienes, 1-4, previously identified in termite Prorhinotermes simplex cuticular hydrocarbons, were efficiently synthesized according Peterson-Hudrlik olefination procedure in high stereoisomeric purity using syn and anti elimination of erythro alkenyl-beta-hydroxysilanes (15 and 17). These (Z)- and (E)-alkenyl-beta-hydroxysilanes are available from regioselective opening of (1R*,2S*)-1,2-epoxy-1-trimethylsilylpentadecane 13 with corresponding (Z)- and (E)-dodec-1-enyl cuprates (14 and 16). Stereoisomeric purity of obtained dienes 1-4 was higher than 95% (C-13 NMR).