Stereoselective total synthesis of diplodialide A
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ORIGINAL PAPER
Stereoselective total synthesis of diplodialide A Kolluri Ramakrishna1 · Reddymasu Sreenivasulu2 · Mandava Venkata Basaveswara Rao3 · Siddaiah Vidavalur1 · Boggu Jagan Mohan Reddy4 Received: 19 April 2020 / Accepted: 16 September 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
Abstract An efficient stereoselective total synthesis of Diplodialide A has been achieved from inexpensive and commercially available starting material (R)-propylene oxide. This linear synthesis utilizes Wittig reaction, alkylation of 1,3-dithiane and Yamaguchi macrolactonization as key steps. Graphic abstract
Keywords (R)-propylene oxide · Wittig reaction · Alkylation of 1,3-dithiane · Yamaguchi · Macrolactonization · Diplodialide A
Introduction The molecules containing medium-sized-ring systems (8–11 atoms in the ring) (Drager et al. 1996; Ferraz et al. 2007; Riatto et al. 2008) have attracted considerable attention from Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01365-1) contains supplementary material, which is available to authorized users. * Siddaiah Vidavalur [email protected] * Boggu Jagan Mohan Reddy [email protected] 1
Department of Organic Chemistry, Food, Drugs and Water, Andhra University, Visakhapatnam, Andhra Pradesh 530003, India
2
Department of Chemistry, University College of Engineering (Autonomous), Jawaharlal Nehru Technological University, Kakinada, Andhra Pradesh 533003, India
3
Department of Chemistry, Krishna University, Machilipatnam, Andhra Pradesh 521001, India
4
Department of Chemistry, Adikavi Nannaya University, Rajamahendravaram, Andhra Pradesh 533296, India
synthetic as well as bioorganic chemists due to their interesting structures and potent biological activities. Ten-membered decanolides can be integrated into a range of various secondary metabolites from natural origin bearing lactone moieties (Omura 1986). However, medium-sized lactones, especially ten-membered decanolides, have drawn little attention to date. The first examples of decanolides to be discovered, the diplodialides A–D (1a–1d) were reported by Ishida and Wada in 1975 (Ishida and Wada 1975). Diplodialides (A (1a), B (1b), C (1c), and D (1d)) are the first ten-membered lactone pentaketides (Fig. 1), which were isolated from the plant pathogenic fungus Diplodia pinea (IFO 6472) by Wada and Ishida (Ishida and Wada 1975; Wada and Ishida 1976). These metabolites of microbial origin exhibit biological properties as steroid-hydroxylase inhibitors. Diplodialides exhibit various biological activities, in particular, diplodialide A display significant inhibitory activity against progesterone 11α-hydroxylase in vegetable cell cultures of Rhizopus stolonifer at 125 ppm. The absolute stereochemistries of diplodialides were assigned as (9R)-1a, (3S, 9R)-1b, and (3R, 9R)-1c by Wada and Ishida (Wada and Ishida 1979).
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Chemical Papers
Fig. 1 Structures of diplodialide A, diplodialide B, diplodialide C and dip
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