TY - JOUR
T1 - Unified Total Synthesis of Madangamines A, C, and E
AU - Suto, Takahiro
AU - Yanagita, Yuta
AU - Nagashima, Yoshiyuki
AU - Takikawa, Shinsaku
AU - Kurosu, Yasuhiro
AU - Matsuo, Naoya
AU - Sato, Takaaki
AU - Chida, Noritaka
N1 - Funding Information:
This research was supported by the Otsuka Pharmaceutical Co. Award in Synthetic Organic Chemistry, Japan. We thank Prof. Raymond J. Andersen, The University of British Columbia, Canada, for providing 1H and 13C NMR spectra of madangamine alkaloids and precious advice. Synthetic assistance from T. Matsumoto, S. Hiraoka, and Y. Komiya is gratefully acknowledged.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/3/1
Y1 - 2017/3/1
N2 - A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.
AB - A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.
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U2 - 10.1021/jacs.7b00807
DO - 10.1021/jacs.7b00807
M3 - Article
C2 - 28190360
AN - SCOPUS:85014205457
VL - 139
SP - 2952
EP - 2955
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 8
ER -