Total Synthesis of (±)-γ-Rubromycin on the Basis of Two Aromatic Pummerer-Type Reactions

• Published in: Angewandte Chemie (International ed.) Vol. 46; no. 39; pp. 7458 - 7461
• Main Authors: Akai, Shuji, Kakiguchi, Keisuke, Nakamura, Yuka, Kuriwaki, Ikumi, Dohi, Toshifumi, Harada, Shusaku, Kubo, Ozora, Morita, Nobuyoshi, Kita, Yasuyuki
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley-VCH Verlag 01.01.2007; WILEY-VCH Verlag; WILEY‐VCH Verlag; Wiley
• Subjects: Biological Products - chemistry; Chemistry; Chemistry, Multidisciplinary; Furans - chemistry; Molecular Structure; natural products; Physical Sciences; Pummerer reaction; Quinones - chemical synthesis; Quinones - chemistry; rearrangement; Science & Technology; Spiro Compounds - chemistry; spiroketals; total synthesis; Pummerer reaction; EFFICIENT SYNTHESIS; SPIROKETAL SKELETON; CARBON BOND FORMATION; natural products; P-SULFINYLPHENOLS; spiroketals; STREPTOMYCES SP MJ929-SF2; CONVERGENT ROUTE; PURPUROMYCIN; DNA HELICASE; total synthesis; HELIQUINOMYCIN; rearrangement; GAMMA-RUBROMYCIN
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200702382

Double or nothing: In a convergent synthesis of the title compound, a potent inhibitor of human telomerase, two different aromatic Pummerer‐type reactions were employed to construct the pivotal bisbenzannelated spiroketal skeleton from the two fragments shown in the scheme. This methodology offers convenient access to a wide range of substituted bisbenzannelated spiroketals from naphthol derivatives. MOM=methoxymethyl.