In:
Helvetica Chimica Acta, Wiley, Vol. 60, No. 4 ( 1977-06), p. 1262-1272
Abstract:
Incorporation experiments with ( 3 H and 14 C) doubly labelled farnesols into cantharidin After injection of 11′, 12‐[ 3 H]‐7‐[ 14 C]‐farnesol or 11′, 12‐[ 3 H]‐5,6‐[ 14 C]‐farnesol, the 3 H‐label is located specifically in the C(9)‐methyl‐group of cantharidin, whereas the 14 C‐labelling pattern follows an incorporation via acetic acid (Scheme 4) . C‐Atoms 5, 6 and 7 from the middle part of the farnesol molecule are utilized for cantharidin biosynthesis to an extent that is about 2.1–11% of the incorporation rate of the methyl groups C(11′) and C(12), depending on the position of the 14 C‐label in farnesol. These results confirm our earlier hypothesis [1] that the C 10 ‐molecule cantharidin is biosynthesized from the C 15 ‐precursor farnesol which is cleaved between C(1)–C(2), C(4)–C(5), and C(7)–C(8). The synthesis of 7‐[ 14 C]‐farnesol and of 5,6‐[ 14 C]‐farnesol is described.
Type of Medium:
Online Resource
ISSN:
0018-019X
,
1522-2675
DOI:
10.1002/hlca.19770600416
Language:
English
Publisher:
Wiley
Publication Date:
1977
detail.hit.zdb_id:
74-7
detail.hit.zdb_id:
1475013-2
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