Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates

Ana R. Rodriguez; Bernd W. Spur

doi:10.1016/j.tetlet.2015.09.020

Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates

Ana R. Rodriguez
, Bernd W. Spur

Cell Biology

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

21 Scopus citations

Abstract

The stereospecific total synthesis of the pro-resolving and tissue-regenerative Protectin sulfido-conjugates: 16R,17S-PCTR1, 16R,17S-PCTR2, and 16R,17S-PCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 16S,17S-epoxy-Protectin methyl ester was synthesized using the Sharpless catalytic asymmetric epoxidation to generate the chiral centers at C16 and C17. A Cs₂CO₃ promoted coupling provided the skipped diyne intermediate. Wittig reactions and epoxide opening with glutathione, l-cysteinylglycine, and l-cysteine methyl ester hydrochloride, respectively, were the key steps in the synthesis.

Original language	English (US)
Pages (from-to)	5811-5815
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.020
State	Published - Oct 14 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2015.09.020

Cite this

@article{7859f3b604c6447c8a958a8fc1cf0d1b,

title = "Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates",

abstract = "The stereospecific total synthesis of the pro-resolving and tissue-regenerative Protectin sulfido-conjugates: 16R,17S-PCTR1, 16R,17S-PCTR2, and 16R,17S-PCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 16S,17S-epoxy-Protectin methyl ester was synthesized using the Sharpless catalytic asymmetric epoxidation to generate the chiral centers at C16 and C17. A Cs2CO3 promoted coupling provided the skipped diyne intermediate. Wittig reactions and epoxide opening with glutathione, l-cysteinylglycine, and l-cysteine methyl ester hydrochloride, respectively, were the key steps in the synthesis.",

author = "Rodriguez, \{Ana R.\} and Spur, \{Bernd W.\}",

year = "2015",

month = oct,

day = "14",

doi = "10.1016/j.tetlet.2015.09.020",

language = "English (US)",

volume = "56",

pages = "5811--5815",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "42",

}

TY - JOUR

T1 - Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates

AU - Rodriguez, Ana R.

AU - Spur, Bernd W.

PY - 2015/10/14

Y1 - 2015/10/14

N2 - The stereospecific total synthesis of the pro-resolving and tissue-regenerative Protectin sulfido-conjugates: 16R,17S-PCTR1, 16R,17S-PCTR2, and 16R,17S-PCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 16S,17S-epoxy-Protectin methyl ester was synthesized using the Sharpless catalytic asymmetric epoxidation to generate the chiral centers at C16 and C17. A Cs2CO3 promoted coupling provided the skipped diyne intermediate. Wittig reactions and epoxide opening with glutathione, l-cysteinylglycine, and l-cysteine methyl ester hydrochloride, respectively, were the key steps in the synthesis.

AB - The stereospecific total synthesis of the pro-resolving and tissue-regenerative Protectin sulfido-conjugates: 16R,17S-PCTR1, 16R,17S-PCTR2, and 16R,17S-PCTR3, derived from docosahexaenoic acid, has been achieved. The key intermediate 16S,17S-epoxy-Protectin methyl ester was synthesized using the Sharpless catalytic asymmetric epoxidation to generate the chiral centers at C16 and C17. A Cs2CO3 promoted coupling provided the skipped diyne intermediate. Wittig reactions and epoxide opening with glutathione, l-cysteinylglycine, and l-cysteine methyl ester hydrochloride, respectively, were the key steps in the synthesis.

UR - https://www.scopus.com/pages/publications/84941993638

UR - https://www.scopus.com/pages/publications/84941993638#tab=citedBy

U2 - 10.1016/j.tetlet.2015.09.020

DO - 10.1016/j.tetlet.2015.09.020

M3 - Article

AN - SCOPUS:84941993638

SN - 0040-4039

VL - 56

SP - 5811

EP - 5815

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

Total synthesis of pro-resolving and tissue-regenerative Protectin sulfido-conjugates

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this