A stereospecific synthesis of (±)-cocaine

Joseph J. Tufariello; John J. Tegeler; Shing Chun Wong; Sk Asrof Ali

doi:10.1016/0040-4039(78)80029-X

A stereospecific synthesis of (±)-cocaine

Joseph J. Tufariello^*
, John J. Tegeler
, Shing Chun Wong
, Sk Asrof Ali

^*Corresponding author for this work

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

32 Scopus citations

Original language	English
Pages (from-to)	1733-1736
Number of pages	4
Journal	Tetrahedron Letters
Volume	19
Issue number	20
DOIs	https://doi.org/10.1016/0040-4039(78)80029-X
State	Published - 1978
Externally published	Yes

Bibliographical note

Funding Information:
The nitrogen oxygen bond of methiodide adduct -12 was cleaved with zinc and acetic acid to give a 47% yield of ecgonine methyl ester (13). The ir spectrum exhibited strong absorption at 2.60 p confirming the presence of a free hydroxyl group, and a strong band at 5.86 U, attributable to the ester carbonyl stretch. The nmr spectrum displayed the expected three-proton singlet at 61.90 ppm (CH3N) and another at 63.28 ppm (C02CH3). Benzoylation of hydroxyester -13 using the method of de Jong4 provided (+)-cocaine whose ir, nmr, and mass spectra were virtually identical with those of natural (-)-cocaine. Thus, the intramolecular nitrone cyclization has provided the first stereospecific total synthesis of (+)-cocaine. We wish to acknowledge the support obtained from the National Institutes of Health (CA 14611). In addition, we wish to thank Professors E. Leete and H. D, Durst for a small sample of (-)-cocaine.

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/0040-4039(78)80029-X

Cite this

@article{62cc927635ea4f1c846e3427d46a3856,

title = "A stereospecific synthesis of (±)-cocaine",

author = "Tufariello, \{Joseph J.\} and Tegeler, \{John J.\} and Wong, \{Shing Chun\} and Ali, \{Sk Asrof\}",

note = "Funding Information: The nitrogen oxygen bond of methiodide adduct -12 was cleaved with zinc and acetic acid to give a 47\% yield of ecgonine methyl ester (13). The ir spectrum exhibited strong absorption at 2.60 p confirming the presence of a free hydroxyl group, and a strong band at 5.86 U, attributable to the ester carbonyl stretch. The nmr spectrum displayed the expected three-proton singlet at 61.90 ppm (CH3N) and another at 63.28 ppm (C02CH3). Benzoylation of hydroxyester -13 using the method of de Jong4 provided (+)-cocaine whose ir, nmr, and mass spectra were virtually identical with those of natural (-)-cocaine. Thus, the intramolecular nitrone cyclization has provided the first stereospecific total synthesis of (+)-cocaine. We wish to acknowledge the support obtained from the National Institutes of Health (CA 14611). In addition, we wish to thank Professors E. Leete and H. D, Durst for a small sample of (-)-cocaine.",

year = "1978",

doi = "10.1016/0040-4039(78)80029-X",

language = "English",

volume = "19",

pages = "1733--1736",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "20",

}

TY - JOUR

T1 - A stereospecific synthesis of (±)-cocaine

AU - Tufariello, Joseph J.

AU - Tegeler, John J.

AU - Wong, Shing Chun

AU - Ali, Sk Asrof

N1 - Funding Information: The nitrogen oxygen bond of methiodide adduct -12 was cleaved with zinc and acetic acid to give a 47% yield of ecgonine methyl ester (13). The ir spectrum exhibited strong absorption at 2.60 p confirming the presence of a free hydroxyl group, and a strong band at 5.86 U, attributable to the ester carbonyl stretch. The nmr spectrum displayed the expected three-proton singlet at 61.90 ppm (CH3N) and another at 63.28 ppm (C02CH3). Benzoylation of hydroxyester -13 using the method of de Jong4 provided (+)-cocaine whose ir, nmr, and mass spectra were virtually identical with those of natural (-)-cocaine. Thus, the intramolecular nitrone cyclization has provided the first stereospecific total synthesis of (+)-cocaine. We wish to acknowledge the support obtained from the National Institutes of Health (CA 14611). In addition, we wish to thank Professors E. Leete and H. D, Durst for a small sample of (-)-cocaine.

PY - 1978

Y1 - 1978

UR - https://www.scopus.com/pages/publications/0010482582

U2 - 10.1016/0040-4039(78)80029-X

DO - 10.1016/0040-4039(78)80029-X

M3 - Article

AN - SCOPUS:0010482582

SN - 0040-4039

VL - 19

SP - 1733

EP - 1736

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -