TY - JOUR AU - Nakamura, Hugh; Kawakami, Manami; Tsukano, Chihiro; Takemoto, Yoshiji TI - Construction of the ACDE Ring System of Calyciphylline A-type Alkaloids via Intramolecular Diels–Alder Reaction of a Tetrasubstituted Olefin SN - 0936-5214 SN - 1437-2096 PY - 2019 JO - Synlett JF - Synlett LA - EN VL - 30 IS - 20 SP - 2253 EP - 2257 ET - 2019/11/07 DA - 2019/12/02 KW - Daphniphyllum alkaloid KW - calyciphylline A KW - Diels–Alder reaction KW - tetrasubstituted olefin AB - A concise synthesis of the ACDE tetracyclic ring system of calyciphylline A-type alkaloids was investigated. The intramolecular Diels–Alder reaction of a tetrasubstituted olefin with furan enabled the construction of the ACD ring system bearing two contiguous quaternary carbons in one step, and subsequent intramolecular [3+2] cycloaddition successfully gave the E ring. PB - © Georg Thieme Verlag DO - 10.1055/s-0039-1690267 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0039-1690267 ER -