Concise total synthesis of (-)-myxalamide A.
The MIDA touch: A concise and highly convergent protecting-group-free total synthesis of (-)-myxalamide A involves a stereoselective vinylogous Mukaiyama aldol reaction of a vinylketene silyl N,O-acetal, together with a one-pot Stille/Suzuki-Miyaura cross-coupling reaction using Burke's N-methyliminodiacetic acid (MIDA) boronate to connect left- and right-hand fragments of the molecule (see scheme).
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
Kazuhiro
K
Fujita
Ryosuke
R
Matsui
Takahiro
T
Suzuki
Susumu
S
Kobayashi
D000447:Aldehydes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D016941:Myxococcus xanthus / Q000737:chemistry*; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000900:Anti-Bacterial Agents; D011090:Polyenes; C039622:myxalamid A; C116609:3-hydroxybutanal