Wei Jun, Vander Jagt David L, Royer Robert E, Deck Lorraine M
Department of Chemistry, University of New Mexico, Albuquerque, NM 87131.
Tetrahedron Lett. 2010 Oct 3;51(44):5757-5760. doi: 10.1016/j.tetlet.2010.08.089. Epub 2010 Aug 30.
Hemigossypol (3), a sesquiterpene natural product, was previously isolated from Gossypium barbadense and was shown to display improved anti-fungal activity compared to gossypol (1), the disesquiterpene dimer of hemigossypol (3). Gossypol exhibits multiple biological activities. In order to study whether hemigossypol and it derivatives retain the various bioactivities of gossypol, we developed a short and convenient synthetic scheme to synthesize hemigossypol. This is the first de novo synthesis of this natural product. In addition derivatives of hemigossypol with various 2,5-alkyl substituents were synthesized. Modification of the synthetic scheme also afforded the natural product hemigossylic lactone (4) and its 2,5-substituted derivatives.
半棉酚（3）是一种倍半萜天然产物，先前从海岛棉中分离得到，与半棉酚（3）的双倍半萜二聚体棉酚（1）相比，它显示出更强的抗真菌活性。棉酚具有多种生物活性。为了研究半棉酚及其衍生物是否保留了棉酚的各种生物活性，我们开发了一种简短且便捷的合成方案来合成半棉酚。这是该天然产物的首次从头合成。此外，还合成了具有各种2,5-烷基取代基的半棉酚衍生物。合成方案的改进还得到了天然产物半棉酚内酯（4）及其2,5-取代衍生物。
