Tetrahedron letters

Total synthesis of phenoxan and a related pyrone derivative

Y Ishibashi, S Ohba, S Nishiyama, S Yamamura

Index: Ishibashi, Yasuharu; Ohba, Shigeru; Nishiyama, Shigeru; Yamamura, Shosuke Tetrahedron Letters, 1996 , vol. 37, # 17 p. 2997 - 3000

Full Text: HTML

Citation Number: 35

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Phenoxan, HIV-1 inhibitor isolated from the myxobacteria, has been synthesized in 16 steps starting from ethyl 2-methylacetoacetate. The related isomer corresponding to the oxazole part was also obtained via an orthoester-enediol rearrangement. ... Synthesis of phenoxan ...

 Related Synthetic Route
Ethyl 2-methylacetoacetate Structure

609-14-3

Ethyl 2-methyla...

Ethyl iodide Structure

75-03-6

Ethyl iodide

~70%

2-METHYL-3-OXO-HEXANOIC ACID ETHYL ESTER Structure

29304-40-3

2-METHYL-3-OXO-...

(E)-3-ethyl-6-methoxy-5-methyl-2-(2-(3-methyl-4-phenylbut-3-en-1-yl)-4,5-dihydrooxazol-4-yl)-4H-pyran-4-one Structure

177366-41-5

(E)-3-ethyl-6-m...

~76%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

Ethyl 2-methylacetoacetate Structure

609-14-3

Ethyl 2-methyla...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

2-METHYL-3-OXO-HEXANOIC ACID ETHYL ESTER Structure

29304-40-3

2-METHYL-3-OXO-...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

3-ethyl-6-methoxy-5-methyl-2-vinyl-4H-pyran-4-one Structure

177366-33-5

3-ethyl-6-metho...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

2-(1,2-dihydroxyethyl)-3-ethyl-6-methoxy-5-methyl-4H-pyran-4-one Structure

177366-34-6

2-(1,2-dihydrox...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

N/A Structure

177366-32-4

N/A

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

N/A Structure

177366-31-3

N/A

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

N/A Structure

177366-43-7

N/A

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

2-(1-azido-2-((tert-butyldimethylsilyl)oxy)ethyl)-3-ethyl-6-methoxy-5-methyl-4H-pyran-4-one Structure

177366-44-8

2-(1-azido-2-((...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

2-((tert-butyldimethylsilyl)oxy)-1-(3-ethyl-6-methoxy-5-methyl-4-oxo-4H-pyran-2-yl)ethyl methanesulfonate Structure

177366-38-0

2-((tert-butyld...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

2-(1-amino-2-((tert-butyldimethylsilyl)oxy)ethyl)-3-ethyl-6-methoxy-5-methyl-4H-pyran-4-one Structure

177366-39-1

2-(1-amino-2-((...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

(E)-N-(1-(3-ethyl-6-methoxy-5-methyl-4-oxo-4H-pyran-2-yl)-2-hydroxyethyl)-4-methyl-5-phenylpent-4-enamide Structure

1027322-60-6

(E)-N-(1-(3-eth...

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...

N/A Structure

177366-40-4

N/A

~%

5-ethyl-2-methoxy-3-methyl-6-[2-[(E)-3-methyl-4-phenylbut-3-enyl]-1,3-oxazol-4-yl]pyran-4-one Structure

134332-63-1

5-ethyl-2-metho...


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