New entry to the synthesis of clerodane diterpenes. The first enantioselective syntheses of 7-oxo-kolavenic acid and methyl solidagonate

Authors
Kato, M Kosugi, H Ichiyanagi, T Hagiwara, H Kodaira, A Kusakari, T Suzuki, T Ando, M Lee, J Drechsel, P Vogler, B
Citation
M. Kato et al., New entry to the synthesis of clerodane diterpenes. The first enantioselective syntheses of 7-oxo-kolavenic acid and methyl solidagonate, TETRAHEDRON, 57(39), 2001, pp. 8243-8256
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
39
Year of publication
2001
Pages
8243 - 8256
Database
ISI
SICI code
0040-4020(20010924)57:39<8243:NETTSO>2.0.ZU;2-S
Abstract
Using (1S,5S)-(-)-verbenone (8b), readily obtainable from (+)-nopinone (3), as the chiral source, we have established the general method for preparati on of three kinds of key intermediates, conjugate enones 9 and 10 for the s yntheses of neo-trans-clerodanes and ae C11 for those of neo-cis-clerodanes . Starting with the compound 10, the first enantioselective syntheses of (- )-(5R,8S,9S,10R)-7-oxo-cleroda-3,13E-dien-15-oic cid (7-oxo-kolavenic acid) (1) and solidagonic acid (2) as its methyl ester (48) were achieved. (C) 2 001 Elsevier Science Ltd. All rights reserved.