Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide
Publication type: Journal Article
Publication date: 2002-11-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
The first total synthesis of somamide A (1), an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide, from the marine cyanobacterium Lyngbya majuscula is described. The efficient and stereospecific dehydration of the N-acyl threonine ester using Martin's sulfurane provided the (Z)-2-amino-2-butenoic acid residue. The macrolactamization using FDPP(Ph2P(O)OC6F5), the final installation of the Ahp moiety by oxidation with 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide, and cyclization of the norvaline derivative to the cyclic hemiaminal afforded somamide A (1).
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(4.88%)
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GOST
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Yokokawa F., Shioiri T. Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide // Tetrahedron Letters. 2002. Vol. 43. No. 48. pp. 8673-8677.
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Yokokawa F., Shioiri T. Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide // Tetrahedron Letters. 2002. Vol. 43. No. 48. pp. 8673-8677.
Cite this
RIS
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TY - JOUR
DO - 10.1016/S0040-4039(02)02178-0
UR - https://doi.org/10.1016/S0040-4039(02)02178-0
TI - Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide
T2 - Tetrahedron Letters
AU - Yokokawa, Fumiaki
AU - Shioiri, Takayuki
PY - 2002
DA - 2002/11/01
PB - Elsevier
SP - 8673-8677
IS - 48
VL - 43
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2002_Yokokawa,
author = {Fumiaki Yokokawa and Takayuki Shioiri},
title = {Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide},
journal = {Tetrahedron Letters},
year = {2002},
volume = {43},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/S0040-4039(02)02178-0},
number = {48},
pages = {8673--8677},
doi = {10.1016/S0040-4039(02)02178-0}
}
Cite this
MLA
Copy
Yokokawa, Fumiaki, and Takayuki Shioiri. “Total synthesis of somamide A, an Ahp (3-amino-6-hydroxy-2-piperidone)-containing cyclic depsipeptide.” Tetrahedron Letters, vol. 43, no. 48, Nov. 2002, pp. 8673-8677. https://doi.org/10.1016/S0040-4039(02)02178-0.