Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Sherwood, Alexander; Williamson, Samuel; Johnson, Stephanie; YILMAZ, ANIL; Day, Victor; Prisinzano, Thomas

doi:10.1021/acs.joc.7b02324

Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Sherwood A. M., Williamson S. E., Johnson S. N., YILMAZ A., Day V. W., Prisinzano T. E.

Journal of Organic Chemistry, cilt.83, sa.2, ss.980-992, 2018 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 83 Sayı: 2
Basım Tarihi: 2018
Doi Numarası: 10.1021/acs.joc.7b02324
Dergi Adı: Journal of Organic Chemistry
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.980-992
Trakya Üniversitesi Adresli: Hayır

Özet

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.