Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene

Tetrahedron Asymmetry

Volumn 10, Issue 19, 1999, Pages 3691-3700

  Kato, Tadahiro ^a   Ebihara, Shin Ichi ^a   Furukawa, Tohru ^a   Tanahashi, Hirota ^a   Hoshikawa, Masahiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY 11 DIHYDRONEOCEMBRENE; DITERPENE; GERANIOL; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHLORINATION; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033405870     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00376-6     Document Type: Article

References (14)

1. This constitutes part 59 of the series of cyclization of polyenes. Part 58, see: Kato, T.; Nagae, K.; Hoshikawa, M. Tetrahedron Lett. 1999, 40, 1941-1944.
2. Prestwich, G. D. Biochem. Syst. Ecol. 1979, 7, 211-221.
3. Kato, T.; Tanaka, M.; Hoshikawa, M.; Yagi, M. Tetrahedron Lett. 1998, 39, 7553-7556 and references cited therein.
4. Geranyl acetate 13 and R-(+)-citronellol 15 were, respectively, kindly supplied by Kurarey Co. Ltd and Takasago Perfumery Co. Ltd, to whom we are grateful.
5. For an example, Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526-5528.
6. Bäckvall, J. E.; Séllen, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615-6621.
7. 13C NMR spectra of the crude reaction products.
8. See Ref. 6 and Klaveren, M. V.; Persson, E. S. M.; Grove, D. M.; Bäckvall, J. E.; Koten, G. V. Tetrahedron Lett. 1994, 32, 5931-5934.
9. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156-4158.
10. Kitahara, Y.; Kato, T.; Kobayashi, T.; Moore, B. P. Chem. Lett. 1976, 219-222.
11. Kato, T.; Aoki, M.; Uyehara, T. J. Org. Chem. 1987, 52, 1803-1810.
12. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717-1724.
13. Similar phenomena were observed in the NMR spectra of cis- and trans-alcohols of the cembrene series. The stereochemistry including conformation of the trans alcohol was confirmed from X-ray crystallographic analysis and NMR spectrum [Kato, T.; Kabuto, C.; Kim, K. H.; Takayanagi, H.; Uyehara, T.; Kitahara, Y. Chem. Lett. 1977, 827-830].
14. Harada, N.; Iwabuchi, J.; Yokota, Y.; Uda, H.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 5590-5591.