8-Endo cyclization of (alkoxycarbonyl)methyl radicals: Stereoselective synthesis of (-)-clavukerin A and (-)-11-hydroxyguaiene

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5929-5930

  Lee, Eun ^a   Yoon, Cheol Hwan ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; LIMONENE; METHYL GROUP; NATURAL PRODUCT; RADICAL; SESQUITERPENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CORAL; CYCLIZATION; OXIDATION; POLYMERIZATION; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030581338     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01279-8     Document Type: Article

References (11)

1. 1. Kobayashi, M.; Son, B. W.; Kido, M.; Kyogoku, Y.; Kitagawa, I. Chem. Pharm. Bull. 1983, 31, 2160-2163.
2. 2. a) Kim, S. K.; Pak, C. S. J. Org. Chem. 1991, 56, 6829-6832.
3. b) Asaoka, M.; Kosaka, T.; Itahana, H.; Takei, H. Chem. Lett. 1991, 1295-1298.
4. c) Shimizu, I.; Ishikawa, T. Tetrahedron Lett. 1994, 35, 1905-1908.
5. d) Honda, T.; Ishige, H.; Nagase, H. J. Chem. Soc. Perkin Trans. I 1994, 3305-3310.
6. 3. Lee, E.; Yoon, C. H.; Lee, T. H. J. Am. Chem. Soc. 1992, 114, 10981-10982.
7. 4. Wolinsky, J; Slabaugh, M. R.; Gibson, T. J. Org. Chem. 1964, 29, 3740-3742.
8. 3).
9. 6. (-)-Clavukerin A(1) was obtained in 9 steps from (+)-limonene oxide (34 % overall yield). This is by far the most efficient synthesis.
10. 7. Bohlmann, F; Zdero, C.; Lonitz, M. Phytochemistry; 1977, 16, 575-577.
11. 3).