Total synthesis of angucyclines. 9. An Alternative Biomimetic-Type Synthesis of 8-Deoxytetrangomycin

Karsten Krohn; Nasir Hayat

doi:10.1002/prac.19983400211

Total synthesis of angucyclines. 9. An Alternative Biomimetic-Type Synthesis of 8-Deoxytetrangomycin

Journal für praktische Chemie ◽

10.1002/prac.19983400211 ◽

1998 ◽

Vol 340 (2) ◽

pp. 171-174 ◽

Cited By ~ 4

Author(s):

Karsten Krohn ◽

Nasir Hayat

Keyword(s):

Total Synthesis ◽

Type Synthesis

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ChemInform Abstract: Biomimetic-Type Synthesis of Halogenated Tetrahydrofurans from Laurencia. Total Synthesis of trans-(+)-Deacetylkumausyne.

ChemInform ◽

10.1002/chin.199732197 ◽

2010 ◽

Vol 28 (32) ◽

pp. no-no

Author(s):

T. MARTIN ◽

M. A. SOLER ◽

J. M. BETANCORT ◽

V. S. MARTIN

Keyword(s):

Total Synthesis ◽

Type Synthesis

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Two new diphenyl ethers and a new depside from the lichen Micarea prasina Fr

Australian Journal of Chemistry ◽

10.1071/ch9842349 ◽

1984 ◽

Vol 37 (11) ◽

pp. 2349 ◽

Cited By ~ 28

Author(s):

JA Elix ◽

AJ Jones ◽

LCBJ Lajide ◽

PW James

Keyword(s):

Total Synthesis ◽

Methyl Esters ◽

Sodium Hydride ◽

Hydroxybenzoic Acid ◽

Type Synthesis ◽

Enol Ethers ◽

Diphenyl Ethers ◽

Key Steps ◽

Methoxybenzoic Acid

Two new diphenyl ethers, 4-(2-carboxy-3-heptyl-5-methoxyphenoxy)-2-heptyl-6-hydroxybenzoic acid (micareic acid) (13), 4-(2-carboxy-3-heptyl-5-methoxyphenoxy)-2-heptyl-6-hydroxy-3-methoxybenzoic acid (methoxymicareic acid) (27) and a new depside, 4-(2-heptyl-6-hydroxy-4-methoxybenzoyloxy)- 2-heptyl-6-hydroxybenzoic acid (prasinic acid) (34) have been detected in chemical races of the lichen Micarea prasina Fr. and isolated and characterized as the corresponding methyl esters. The structure of the latter compounds has been confirmed by total synthesis. The key steps in the synthesis of the diphenyl ethers (14), (26) involved Ullmann-like condensation between the 3-chloro 2-enone (17) and the phenols (11), (31), and subsequent aromatization of the enol ethers (23) and (32). A biomimetic-type synthesis of methyl micareate (48) has also been achieved by treatment of the depside (33) with sodium hydride in dimethylformamide.

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