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45.30.1.1.1.3 Variation 3: Suzuki Coupling

DOI: 10.1055/sos-SD-045-01426

Koo, S.Science of Synthesis, (2010451356.

The merits of the Suzuki coupling are ready availability of stereodefined nontoxic boronic acid reagents, reactivity in aqueous media, and compatibility with a diverse range of functional groups. The Suzuki coupling for the synthesis of natural products such as (+)-fostriecin,[‌35‌] restrictinol,[‌36‌] and β-parinaric acid[‌37‌] is exemplified in Scheme 6. The (Z)-dienylboronate 29, which is coupled with vinyl bromide 28 to give diol 30, can be obtained by rhodium-mediated trans addition of pinacolborane to the terminal acetylene of the corresponding enyne (Scheme 6).[‌38‌] On the other hand, hydroboration of the terminal acetylene with catecholborane followed by hydrolysis affords the (E)-dienylboronic acid 31 (Scheme 6). N-Methyliminodiacetic acid (MIDA) protected haloboronic acid 32 is highly stable to purification and storage, and can be utilized in iterative Suzuki coupling reactions. The MIDA-protected haloboronic acid is inert to Buchwalds anhydrous Suzuki coupling conditions,[‌39‌] thus enabling a selective coupling at the vinyl chloride moiety to produce trienylboronate 33 (Scheme 6). The N-methyliminodiacetic acid (MIDA) protecting group can be easily removed under mild aqueous basic conditions, and subsequent coupling with (9E)-10-iododec-9-enoic acid provides β-parinaric acid (34).

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