Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin

Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22–C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was construc...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 9; pp. 2248 - 2251
Main Authors Suzuki, Ai, Sasaki, Mai, Nakagishi, Tetsuya, Ueda, Tsuyoshi, Hoshiya, Naoyuki, Uenishi, Jun’ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GONIOTHALAMUS-GIGANTEUS
THF
(6S,7S,9R,10R)-6,9-EPOXYNONADEC-18-ENE-7,10-DIOL
OXIDATIVE POLYCYCLIZATIONS
ORGANOMETALLIC REAGENTS
EFFICIENT SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
ANNONACEOUS ACETOGENINS
ASYMMETRIC TOTAL-SYNTHESIS
BROWN ALGA
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Summary:Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22–C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd­(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00877