Construction of three building blocks for the total synthesis of microsclerodermins

Synlett

Volumn , Issue 4, 1999, Pages 453-455

  Sasaki, Shigekazu ^a   Hamada, Yasumasa ^b   Shioiri, Takayuki ^b  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

2 hydroxy 3 Pinanone; Asymmetric alkylation; GABOB; Microsclerodermin (R) tryptophan

Indexed keywords

HEXAPEPTIDE; MICROSCLERODERMIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; GROWTH INHIBITION; SPONGE (PORIFERA);

EID: 0032917841     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2651     Document Type: Article

References (15)

1. Bewley, C. A.; Debitus, C.; Faulkner, D. J. J. Am. Chem. Soc. 1994, 116, 7631-7636.
2. For a recent example, see Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-639; Yokokawa, F.; Shioiri, T. J. Org. Chem. 1998, 63, 8638-8639.
3. For a recent example, see Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627-639; Yokokawa, F.; Shioiri, T. J. Org. Chem. 1998, 63, 8638-8639.
4. Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1997, 38, 3013-3016.
5. A part of this work was presented at First International Peptide Symposium (Kyoto), November 30-December 5, 1997, Abstracts, p. 162 and at 118th Annual Meeting of Pharmaceutical Society of Japan (Kyoto), March 31-April 2, 1998, Abstracts, 2, 24.
6. Oguri, T.; Kawai, N.; Shioiri, T.; Yamada, S. Chem. Pharm. Bull. 1978, 26, 803-808.
7. Irako, N.; Hamada, Y.; Shioiri, T. Tetrahedron 1995, 51, 12731-12744, and references therein.
8. HPLC conditions: Daicel Chiralcel OD, flow rate 1.0 mL/min, hexane-isopropanol=9:1. The reference racemic 2 was prepared analogously from the Schiff base of benzophenone and glycine tert-butyl ester.
9. The configuration of 16 and 17 was determined by the measurement of NOE in the NMR spectra as followed. (Equation Presented)
10. The lactone 3 was obtained as a diastereoisomeric mixture in preference to the (4S,5R)-isomer, and no separation was attempted at this stage.
11. (a) Saito, S.; Hasegawa, T.; Inaba, M.; Nishida, R.; Fujii, T.; Nomizu, S.; Moriwake, T. Chem. Lett. 1984, 1389-1392.
12. (b) Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067-4086.
13. Cheng, Z.; Hamada, Y.; Shioiri, T. Synlett 1997, 109-110.
14. Shioiri, T.; McFarlane, N.; Hamada, Y. Heterocycles 1998, 47, 73-76.
15. Cf. Bellamy, F. D.; Bondoux, M.; Dodey, P. Tetrahedron Lett. 1990, 31, 7323-7326.