Synthetic disproof against the structure proposed for alectrol, the germination stimulant from Vigna unguiculata

• Published in: Tetrahedron letters Vol. 39; no. 33; pp. 6023 - 6026
• Main Authors: Mori, Kenji, Matsui, Junichi, Bando, Masahiko, Kido, Masaru, Takeuchi, Yasutomo
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 13.08.1998; Elsevier
• Subjects: Biologically active compound; Chemistry; Chemistry, Organic; Lactones; NMR; Physical Sciences; Science & Technology; X-Ray crystal structure; Biologically active compound; NMR; X-Ray crystal structure; Lactones; biologically active compound; lactones; (+)-STRIGOL; STRIGOL
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(98)01238-6

Several compounds [(±)- 3a, (±)- 3b, (±)- 10, (±)- 11 and (±)- 12] with the structures related to that ( 3) proposed for alectrol, the germination stimulant, were synthesized. The structure (±)- 3a was solved by X-ray crystallographic analysis. Comparison of the 1H NMR data of the synthetic compounds with those reported for alectrol disproved the correctness of the proposed structure 3. The structure proposed for alectrol was shown to be incorrect by the synthesis and 1H NMR analysis of the related compounds.