Synthesis of Allahabadolactone A

Kongchen Wang; Roderick W. Bates

doi:10.1021/acs.joc.7b02368

Synthesis of Allahabadolactone A

Kongchen Wang, Roderick W. Bates^*

^*Corresponding author for this work

Nanyang Technological University

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

7 Citations (Scopus)

Abstract

A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.

Original language	English
Pages (from-to)	12624-12630
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	82
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.7b02368
Publication status	Published - Dec 1 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Organic Chemistry

Access to Document

10.1021/acs.joc.7b02368

Cite this

@article{889cb1b4a5344fbdb9a7deb84e62e5bc,

title = "Synthesis of Allahabadolactone A",

abstract = "A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.",

author = "Kongchen Wang and Bates, \{Roderick W.\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = dec,

day = "1",

doi = "10.1021/acs.joc.7b02368",

language = "English",

volume = "82",

pages = "12624--12630",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

TY - JOUR

T1 - Synthesis of Allahabadolactone A

AU - Wang, Kongchen

AU - Bates, Roderick W.

PY - 2017/12/1

Y1 - 2017/12/1

N2 - A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.

AB - A synthesis of allahabadolactone A is described employing diastereoselective Diels-Alder and selenocyclization reactions, starting from (R)-citronellal and propylene oxide. The Diels-Alder substrate is built up in an efficient manner by rhodium-catalyzed alkyne hydroboration and palladium-catalyzed coupling reactions of E-1,2-dichloroethene. It is observed that the Diels-Alder reaction only displays high diastereoselectivity when the diene bears an additional alkene substituent but not an alkyne substituent.

UR - http://www.scopus.com/inward/record.url?scp=85036661472&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85036661472&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.7b02368

DO - 10.1021/acs.joc.7b02368

M3 - Article

C2 - 29063754

AN - SCOPUS:85036661472

SN - 0022-3263

VL - 82

SP - 12624

EP - 12630

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Synthesis of Allahabadolactone A

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this