Stereocontrolled total synthesis of the penicillanate ester (2S,5R)-benzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylate

Anthony G.M. Barrett; Minn-Chang Cheng; Santi Sakdarat; Christopher D. Spilling; Sven J. Taylor

doi:10.1016/S0040-4039(01)80395-6

Stereocontrolled total synthesis of the penicillanate ester (2S,5R)-benzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylate

Anthony G.M. Barrett, Minn-Chang Cheng, Santi Sakdarat, Christopher D. Spilling, Sven J. Taylor

Research output: Contribution to journal › Article › peer-review

Original language	American English
Journal	Tetrahedron Letters
Volume	30
DOIs	https://doi.org/10.1016/S0040-4039(01)80395-6
State	Published - Jan 1 1989
Externally published	Yes

Disciplines

Organic Chemistry
Chemistry

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@article{68d396abf81c42c59e0e47be774caeb5,

title = "Stereocontrolled total synthesis of the penicillanate ester (2S,5R)-benzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylate",

author = "Barrett, {Anthony G.M.} and Minn-Chang Cheng and Santi Sakdarat and Spilling, {Christopher D.} and Taylor, {Sven J.}",

note = "(3R)-4-Acetoxy-3-trimethylsilyl-2-azetidinone, was converted into optically pure benzyl penicillanate in seven steps (22%) using (benzyloxy)nitromethane as a reagent for ring annulation. Benzyl penicillanate was prepared in seven steps from (3R)-4-acetoxy-3-trimethylsilyl-2-azetidinone using (benzyloxy)nitromethane for bicyclic ring annulation. Recommended articles Citing articles (0)",

year = "1989",

month = jan,

day = "1",

doi = "10.1016/S0040-4039(01)80395-6",

language = "American English",

volume = "30",

journal = "Tetrahedron Letters",

}

TY - JOUR

T1 - Stereocontrolled total synthesis of the penicillanate ester (2S,5R)-benzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylate

AU - Barrett, Anthony G.M.

AU - Cheng, Minn-Chang

AU - Sakdarat, Santi

AU - Spilling, Christopher D.

AU - Taylor, Sven J.

N1 - (3R)-4-Acetoxy-3-trimethylsilyl-2-azetidinone, was converted into optically pure benzyl penicillanate in seven steps (22%) using (benzyloxy)nitromethane as a reagent for ring annulation. Benzyl penicillanate was prepared in seven steps from (3R)-4-acetoxy-3-trimethylsilyl-2-azetidinone using (benzyloxy)nitromethane for bicyclic ring annulation. Recommended articles Citing articles (0)

PY - 1989/1/1

Y1 - 1989/1/1

UR - https://www.sciencedirect.com/science/article/pii/S0040403901803956

U2 - 10.1016/S0040-4039(01)80395-6

DO - 10.1016/S0040-4039(01)80395-6

M3 - Article

VL - 30

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

Stereocontrolled total synthesis of the penicillanate ester (2S,5R)-benzyl 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylate

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