Synthesis of the H ring of gambierol

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6373-6376

  Kadota, Isao ^a   Ohno, Akio ^a   Matsukawa, Yasuhisa ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYRIBOSE; ALDEHYDE; GAMBIEROL; ORGANOTIN COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

EID: 0032572911     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01312-4     Document Type: Article

References (14)

1. (1) Kadota, I.; Park, C.-H.; Ohtaka, M.; Oguro, N. Yamamoto, Y. Tetrahedron Lett. the first of three contiguous papers in this issue.
2. (2) Kadota, I.; Kadowaki, C.; Yoshida, N. Yamamoto, Y. Tetrahedron Lett. the second of three contiguous papers in this issue.
3. (3) (a) Yamamoto, Y.; Yamada, J.; Kadota, I. Tetrahedron Lett. 1991, 32, 7069-7072.
4. (b) Gevorgyan, V.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1993, 34, 1313-1316.
5. (c) Kadota, I.; Kawada, M.; Gevorgyan, V.; Yamamoto, Y. J. Org. Chem. 1997, 62, 7439-7446.
6. (4) Nicolaou, K. C.; Veale, C. A.; Hwang, C.-K.; Hutchinson, J.; Prasad, C. V. C.; Ogilvie, W. W. Angew, Chem., Int. Ed. Engl. 1991, 30, 299-303.
7. (5) Ziokin, R. E.; Natale, N. R.; Taffer, I. M.; Hutchins, R. O. Synthesis 1980, 1035-1037.
8. (6) Feng, F.; Murai, A. Chem. Lett. 1992, 1587-1590.
9. (7) Ramirez, F.; Desai, N. B.; MaKeelvie, N. J. Am. Chem. Soc. 1962, 84, 1745-1747.
10. (8) (a) Uenishi, J.; Kawahama, R.; Yonemitsu, O. J. Org. Chem. 1996, 61, 5716-5717.
11. (b) Uenishi, J.; Kawahama, R.; Shiga, Y.; Yonemitsu, O. Tetrahedron Lett. 1996, 37, 6759-6762.
12. 4 mediated cis-allylstannylation of acetylene as shown below. (equation presented) For the trans-selective allylstannylation of alkynes, see: Asao, N.; Matsukawa, Y.; Yoshinori, Y. J. Chem. Soc., Chem. Commun. 1996, 1513-1514.
13. (10) For the use of copper salts in Stille coupling, see: Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
14. 3CN) δ 7.46-7.42 (m, 2H), 7.40-7.35 (m, 3H), 6.52-6.47 (m, 1H), 6.44-6.38 (m, 1H), 5.85 (dddd, J = 17.2, 10.2, 6.3, 6.3 Hz, 1H), 5.80 (dd, J = 12.8, 2.9 Hz, 1H), 5.61-5.55 (m, 1H), 5.55 (dd, J = 12.8, 2.0 Hz, 1H), 5.51-5.46 (m, 1H), 5.50 (s, 1H), 5.06 (dddd, J = 17.2, 1.9, 1.7, 1.7 Hz, 1H), 4.99 (dddd, J = 10.2, 1.9, 1.7, 1.7 Hz, 1H), 4.47 (brd, J = 7.6 Hz, 1H), 4.42-4.38 (m, 1H), 4.12 (ddd, J = 8.2, 8.2, 5.0 Hz, 1H), 3.64-3.56 (m, 2H), 2.98-2.94 (m, 2H), 2.74 (s, 1H), 1.26 (s, 3H).