The First Total Synthesis of (±) Cyclophostin and (±) Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase

Raj K. Malla; Saibal Bandyopadhyay; Christopher D. Spilling; Supratik Dutta; Cynthia M. Dupureur

doi:10.1021/ol200991x

The First Total Synthesis of (±) Cyclophostin and (±) Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase

Raj K. Malla, Saibal Bandyopadhyay, Christopher D. Spilling, Supratik Dutta, Cynthia M. Dupureur

University of Missouri-St. Louis

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

Original language	American English
Journal	Organic Letters
Volume	13
DOIs	https://doi.org/10.1021/ol200991x
State	Published - Jun 17 2011

Disciplines

Biochemistry
Organic Chemistry

Access to Document

10.1021/ol200991xLicense: Unspecified

Cite this

@article{eb9d84b498ed48639f55d142b8bac112,

title = "The First Total Synthesis of (±) Cyclophostin and (±) Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase",

author = "Malla, {Raj K.} and Saibal Bandyopadhyay and Spilling, {Christopher D.} and Supratik Dutta and Dupureur, {Cynthia M.}",

note = "Cyclophostin, a structurally unique and potent naturally occurring acetyl cholinesterase (AChE) inhibitor, and its unnatural diastereomer were prepared in 6 steps and 15% overall yield from hydroxymethyl butyrolactone. The unnatural diastereomer of cyclophostin was converted into cyclipostin P, a potent naturally occurring hormone sensitive lipase (HSL) inhibitor, using a one pot dealkylation-alkylation process.",

year = "2011",

month = jun,

day = "17",

doi = "10.1021/ol200991x",

language = "American English",

volume = "13",

journal = "Organic Letters",

}

TY - JOUR

T1 - The First Total Synthesis of (±) Cyclophostin and (±) Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase

AU - Malla, Raj K.

AU - Bandyopadhyay, Saibal

AU - Spilling, Christopher D.

AU - Dutta, Supratik

AU - Dupureur, Cynthia M.

N1 - Cyclophostin, a structurally unique and potent naturally occurring acetyl cholinesterase (AChE) inhibitor, and its unnatural diastereomer were prepared in 6 steps and 15% overall yield from hydroxymethyl butyrolactone. The unnatural diastereomer of cyclophostin was converted into cyclipostin P, a potent naturally occurring hormone sensitive lipase (HSL) inhibitor, using a one pot dealkylation-alkylation process.

PY - 2011/6/17

Y1 - 2011/6/17

UR - http://pubs.acs.org/doi/abs/10.1021/ol200991x

UR - https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3129627/

U2 - 10.1021/ol200991x

DO - 10.1021/ol200991x

M3 - Article

VL - 13

JO - Organic Letters

JF - Organic Letters

ER -

The First Total Synthesis of (±) Cyclophostin and (±) Cyclipostin P: Inhibitors of the Serine Hydrolases Acetyl Cholinesterase and Hormone Sensitive Lipase

Disciplines

Access to Document

Other files and links

Cite this