synargentolide A | 212266-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: synargentolide A
• 英文别名: 6R-[4′R,5′R,6′R-(triacetyloxy)-1E-heptenyl]-5,6-dihydro-2H-pyran-2-one；(6R)-6-[(4R,5R,6R)-4,5,6-triacetyloxy-1-(E)-heptenyl]-5,6-dihydro-2H-pyran-2-one；(1R,2R,4E)-2-(acetyloxy)-1-[(1R)-1-(acetyloxy)ethyl]-5-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-4-pentenyl acetate；(1R,2R,4E)-2-acetoxy-1-[(1R)-1-acetoxyethyl]-5-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl acetate；(2R,3R,4R,6E)-7-[(2R)-3,6-dihydro-6-oxo-2H-pyran-2-yl]hept-6-ene-1,3,4-triyl triacetate；(2R,3R,4R,E)-7-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)hept-6-ene-2,3,4-triyl triacetate；(6R)-5,6-dihydro-6-[(1E,4R,5R,6R)-4,5,6-tris(acetyloxy)hept-1-en-1-yl]-2H-pyran-2-one；[(E,2R,3R,4R)-3,4-diacetyloxy-7-[(2R)-6-oxo-2,3-dihydropyran-2-yl]hept-6-en-2-yl] acetate
• CAS: 212266-10-9
• 化学式: C₁₈H₂₄O₈
• 分子量: 368.384
• InChiKey: MCXAMJAYXFXQPD-DYOCFBNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethane-1,2-diol 在 咪唑 、 2,6-二甲基吡啶 、 Grubbs catalyst first generation 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 双氧水 、 碘 、 palladium(II) hydroxide 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 二正丁基氧化锡 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 sodium hydroxide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 、 正戊烷 、 苯 为溶剂， 反应 48.58h， 生成 synargentolide A
  参考文献：
  名称：

  Total synthesis of (+)-synargentolide A

  摘要：

  The highly stereoselective total synthesis of polyacetate alpha,beta-unsaturated delta-lactone natural product (+)-synargentolide A has been accomplished from inexpensive D-1,5-gluconolactone. Key reactions involved in the synthesis are hydroboration, Wittig olefination, Brown's asymmetric allylation, and a ring closing metathesis reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.021

文献信息

• First stereoselective synthesis of synargentolide A and revision of absolute stereochemistry
  作者：Gowravaram Sabitha、Peddabuddi Gopal、C. Nagendra Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2009.08.109

  日期：2009.11

  The first stereoselective total synthesis of synargentolide A isolated from Syncolostemon argenteus has been achieved from commercially available (R)-benzyl glycidyl ether using Sharpless asymmetric epoxidation and cross-metathesis reactions as the key steps. Comparing the spectral data of the synthesized and naturally occurring synargentolide A, the C4′ and C6′- stereogenic centers of the natural

  从Syncolostemon argenteus分离出的香根草素A的第一个立体选择性全合成已使用Sharpless不对称环氧化和交叉复分解反应为关键步骤，从市售（R）-苄基缩水甘油醚中获得。比较合成的和天然存在的同化内酯A的光谱数据，天然同化内酯A的C4'和C6'-立体中心被分配了校正的反关系。
• A Concise Stereoselective Total Synthesis of Synargentolide A from 3,4,6-Tri-O-acetyl-d-glucal
  作者：Gowravaram Sabitha、S. Reddy、Atla Raju、Jhillu Yadav

  DOI：10.1055/s-0030-1258458

  日期：2011.4

  highly stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone synargentolide A is described from the chiral starting material 3,4,6-tri-O-acetyl-d-glucal. Key steps of the synthesis are lactol opening, Brown’s asymmetric allylation, and a ring-closing metathesis (RCM) reaction. 3,4,6-tri-O-acetyl-d-glucal - δ-lactones - synargento­lide - Brown’s allylation - RCM

  天然存在的，α，β不饱和内酯synargentolide A的短且高立体选择性合成，从手性起始材料描述3,4,6-三ö乙酰基d -glucal。合成的关键步骤是乳糖醇开环，布朗的不对称烯丙基化和闭环复分解（RCM）反应。 3,4,6-三Ø乙酰基d -glucal - δ内酯- synargentolide -布朗的烯丙基- RCM
• An Efficient Stereoselective Total Synthesis of Synargentolide A and Its Epimer
  作者：Biswanath Das、Penagaluri Balasubramanyam、Boyapati Veeranjaneyulu、Gandolla Chinna Reddy

  DOI：10.1002/hlca.201000342

  日期：2011.5

  The stereoselective total synthesis of a naturally occurring α‐pyrone (=2H‐pyran‐2‐one) derivative, synargentolide A (1), and of its epimer 2 (with the originally proposed structure of synargentolide A) was efficiently accomplished involving D‐tartaric acid as the starting material and an olefin cross‐metathesis reaction as the key step.

  有效地完成了涉及D的自然存在的α-吡喃酮（= 2 H-吡喃-2-酮）衍生物synargentolide A（1）及其差向异构体2的立体选择性全合成。酒石酸为起始原料，烯烃交叉复分解反应为关键步骤。
• Stereoselective total synthesis of (+)-synargentolide A
  作者：Kavirayani R. Prasad、Kamala Penchalaiah

  DOI：10.1016/j.tetasy.2010.11.005

  日期：2010.12

  The stereoselective synthesis of synargentolide A, a polyhydroxy delta-lactone, has been accomplished from tartaric acid. The key steps in the synthesis involve Keck and Brown allylations and ring closing metathesis. (C) 2010 Elsevier Ltd. All rights reserved.
• An efficient synthesis of synargentolide A from d-mannitol
  作者：Ahmed Kamal、Moku Balakrishna、Papagari Venkat Reddy、Shaikh Faazil

  DOI：10.1016/j.tetasy.2010.10.001

  日期：2010.10

  An efficient synthesis of synargentolide A is described by using D-mannitol and D-malic acid The key features of the synthetic strategy include Wittig olefination ring closing-metathesis reaction and cross-metathesis reaction for the formation of synargentolide A (C) 2010 Elsevier Ltd All rights reserved