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 - Satou, Takaaki
AU - Chida, Noritaka
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 -