The efficient stereoselective synthesis of (2S,3R,4S,5S,6S,11E)3-amino- 6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD), a component of microsclerodermins of marine sponge origin, as its protected form

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3187-3190

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

^a NAGOYA CITY UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

Author keywords

Addition reactions; Aldol reactions; Amino acid and derivatives; Marine metabolites

Indexed keywords

3 AMINO 6 METHYL 12 (4 METHOXYPHENYL) 2,4,5 TRIHYDROXYDODEC 11 ENOIC ACID; AMINO ACID DERIVATIVE; MICROSCLERODERMIN A; MICROSCLERODERMIN B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SPONGE (PORIFERA); STEREOCHEMISTRY; SYNTHESIS;

EID: 0033574446     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00411-6     Document Type: Article

References (9)

1. (a) Bewley, C. A.; Debitus, C.; Faulkner, D. J. J. Am. Chem. Soc. 1994, 116, 7631-7636.
2. (b) Recently, microsclerodermins C, D, and E were isolated from two species of lithistid sponges from the Visayan Islands, Philippines. See Schmidt, E. W.; Faulkner, D. J. Tetrahedron 1998, 54, 3043-3056.
3. For our recent work in this area, see Yokokawa, F.; Shioiri, T. J. Org. Chem. 1998, 63, 8638-8639.
4. A part of this work was presented at the First International Peptide Symposium Held in Kyoto, Japan, on November 30-December 5, 1997 and at the 35th Japanese Peptide Symposium Held in Saga, Japan, onOctober 7-9, 1998.
5. A part of this work was presented at the First International Peptide Symposium Held in Kyoto, Japan, on November 30-December 5, 1997 and at the 35th Japanese Peptide Symposium Held in Saga, Japan, on October 7-9, 1998.
6. Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1997, 38, 3013-3016.
7. Negishi, E.; Takahashi, T.; Baba, S.; Horn, D. E. V.; Okukado, N. J. Am. Chem. Soc. 1987, 709, 2393-2401.
8. D 20 and ent-20 unambiguously revealed the absolute configurations. (Equation Presented)
9. 9: C, 67.76; H, 8.15; N, 2.14. Found: C, 67.49; H, 8.07; N, 2.12.