A New and Effective Approach to the Synthesis of Sulforaphane

Author(s): Duy-Viet Vo, Van-Dat Truong, Thanh-Dao Tran, Van-Thanh-Nhan Do, Ngoc-Tuan-Anh Pham, Khac-Minh Thai.

Journal Name: Letters in Organic Chemistry

Volume 13 , Issue 1 , 2016

Submit Manuscript
Submit Proposal

Graphical Abstract:


Abstract:

Background: Sulforaphane [1-isothiocyanato-(4-methylsulfinyl)butane] identified from Brassicaceae appears to possess health benefits such as activities against breast, skin and prostate cancer and diabetes. in vitro and in vivo    studies provide evidence that it can provide protection at every stage of cancer progression. Sulforaphane was firstly synthesized by Von Schmidt and P.Karrer in 1948 via phthalimide route but after Zhang and co-worker reported its bioactivity in 1992, the chemical synthesis of sulforaphane by alternate route has attracted several research groups in the past 20 years .

Methods: The synthesis started with the preparation of -methylthiolanium tetrafluoroborate by sonication of thiolane (1) with methyl iodide followed by anionic metathesis with NaBF4 in -butanol to give thiolanium tetrafluorborate (2). The ring opening of 2 by SN2 is conducted in 16 hours at 60 °C (as indicated by TLC) to obtain 1-azido-(4- methylsulfinyl)butane (3). Conversion 3 into Erucin (4) was successfully obtained by Staudinger reaction, followed by oxidation of 4 in transition metal-free condition (H2O2/ glacial acetic acid) to give sulforaphane in racemic form.

Results: Sulforaphane was obtained with 41% yield overall via only four steps with high purity without column chromatography. The approach not only opened up a new synthetic pathway to this naturally occurring isothiocyanate and its analogues, but also suggested a possible solution for converting by-products in petroleum refining processes into useful compounds.

Conclusion: Sulforaphane was successfully synthesized from thiolane, a waste product in petroleum processing in a simpler and more efficient fashion, eco-friendy approach. All products were obtained in high yield and high purity. In comparison with previously reported strategies, this new approach is believed to be the shortest and the most efficient synthetic route to date.

Keywords: Brassicaceae, cancer prevention, isothiocyanate, sulforaphane, thiolane, thiolanium salt.

Rights & PermissionsPrintExport Cite as


Article Details

VOLUME: 13
ISSUE: 1
Year: 2016
Page: [7 - 10]
Pages: 4
DOI: 10.2174/1570178611666151015214407

Article Metrics

PDF: 106
HTML: 5
EPUB: 1
PRC: 1